Herbicidal sulphonylamino(thio)carbonyl compounds

ABSTRACT

The invention relates to novel sulphonylamino(thio)carbonyl compounds of the formula (I),                    
     in which 
     A represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl, 
     Q represents oxygen or sulphur, 
     R 1  represents hydrogen or formyl or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl, 
     R 2  represents cyano or halogen or represents in each case optionally substituted alky, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, and 
     R 3  represents in each case optionally substituted heterocyclyl having 5 ring members of which at least one is oxygen, sulphur or nitrogen and from one to three further ring members can be nitrogen, 
     and salts of compounds of the formula (I), 
     the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide being excluded by disclaimer; 
     and also to processes and novel intermediates for the preparation of the novel substances and to their use as herbicides.

This application is a division of application Ser. No. 09/223,246, filed Dec. 30, 1998, now U.S. Pat. No. 6,251,831, which is a continuation of application Ser. No. 09/006,686, filed Jan. 8, 1998, now abandoned, which is a continuation-in-part of PCT/EP96/02826, filed Jun. 28, 1996.

The invention relates to novel sulphonylamino(thio)carbonyl compounds, to a number of processes and to novel intermediates for their preparation, and to their use as herbicides.

It is already known that certain sulphonylaminocarbonyl compounds, such as, for example, the compounds 4,5-dimethoxy-2-(2-methoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carbox-amide possess herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE 4029753). The action of these compounds, however, is not in every respect satisfactory.

The novel sulphonylamino(thio)carbonyl compounds have now been found of the general formula (I),

in which

A represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl,

Q represents oxygen or sulphur,

R¹ represents hydrogen or formyl or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl,

R² represents cyano or halogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, and

R³ represents in each case optionally substituted heterocyclyl having 5 ring members of which at least one is oxygen, sulphur or nitrogen and from one to three further ring members can be nitrogen,

and salts of compounds of the formula (I),

the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamiide being excluded by disclaimer.

The novel sulphonylamino(thio)carbonyl compounds of the general formula (I) are obtained if

(a) aminosulphonyl compounds of the general formula (II)

 in which

A, R¹ and R² have the meanings given above

are reacted with (thio)carboxylic acid derivatives of the general formula (III)

 in which

Q and R³ have the meanings given above and

z represents halogen, alkoxy, aryloxy or arylalkoxy,

optionally in the presence of an acid acceptor and optionally in the presence of a diluent,

or if

(b) sulphonyl iso(thio)cyanates of the general formula (I)

 in which

A, Q, R¹ and R² have the meanings given above

are reacted with heterocycles of the general formula (V)

H—R³  (V)

 in which

R³ has the meaning given above,

optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,

or if

(c) chlorosulphonyl compounds of the general formula (VI)

 in which

A, R¹ and R² have the meanings given above

are reacted with heterocycles of the general formula (V)

H—R³  (V)

 in which

R³ has the meaning given above

and metal (thio)cyanates of the general formula (VII)

MQCN  (VII)

 in which

Q has the meaning given above, and

M represents an alkali metal or alkaline earth metal equivalent,

optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,

or if

(d) chlorosulphonyl compounds of the general formula (VI)

 in which

A, R¹ and R² have the meanings given above

are reacted with (thio)carboxamides of the general formula (VIII)

 in which

Q and R³ have the meanings given above,

optionally in the presence of an acid acceptor and optionally in the presence of a diluent,

or if

(e) sulphonylamino(thio)carbonyl compounds of the general formula (IX)

 in which

A, Q, R¹ and R² have the meanings given above, and

Z represents halogen, alkoxy, aryloxy or arylalkoxy,

are reacted with heterocycles of the general formula (V)

H—R³  (V)

 in which

R³ has the meaning given above,

optionally in the presence of an acid acceptor and optionally in the presence of a diluent,

or if

(f) heterocycles of the general formula (V)

H—R³  (V)

 in which

R³ has the meaning given above,

are reacted with chlorosulphonyl iso(thio)cyanate, optionally in the presence of a diluent, and the adducts formed in this reaction are reacted in situ with benzene derivatives of the general formula (X)

 in which

A, R¹ and R² have the meanings given above,

optionally in the presence of an acid acceptor and optionally in the presence of a diluent,

and, if desired, the compounds of the formula (I) obtained by processes (a), (b), (c), (d), (e) or (f) are converted into salts by customary methods.

The novel sulphonylamino(thio)carbonyl compounds of the general formula (I) are distinguished by a strong herbicidal activity.

The invention relates preferably to compounds of the formula (I) in which

A represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl or C₃-C₆-cycloalkyl,

Q represents oxygen or sulphur,

R¹ represents hydrogen or formyl or represents in each case optionally cyano-, fluoro-, chloro-, bromo-, phenyl- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-carbonyl or C₃-C₆-cycloalkyl-sulphonyl,

R² represents cyano, fluoro, chloro or bromo or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and

R³ represents in each case optionally substituted heterocyclyl of the formulae below,

 in which

Q¹, Q² and Q³ each represent oxygen or sulphur, and

R⁴ represents hydrogen, hydroxyl, amino or cyano, or represents C₂-C₁₀-alkylideneamino, or represents optionally fluoro-, chloro-, bromo-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkoxy, C₁-C₆-alkylamino or C₁-C₆-alkyl-carbonylamino, or represents C₃-C₆-alkenyloxy, or represents di-(C₁-C₄-alkyl)-amino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylamino or C₃-C₆-cycloalkyl-C₁-C₄-alkyl, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl- and/or C₁-C₄-alkoxy-substituted phenyl, phenylamino or phenyl-C₁-C₄-alkyl,

R⁵ represents hydrogen, hydroxyl, mercapto, amino, cyano, fluoro, chloro, bromo or iodo, or represents optionally fluoro-, chloro-, bromo-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, or represents in each case optionally fluoro-, chloro-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆alkylamino or C₁-C₆-alkyl-carbonylamino, or represents C₃-C₆-alkenyloxy, C₃-C₆-alkinyloxy, C₃-C₆-alkenylthio, C₃-C₆-alkinylthio, C₃-C₆-alkenylamino or C₃-C₆-alkinylamino, or represents di-(C₁-C₄-alkyl)-amino, or represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio, C₃-C₆-cycloalkylamino C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkylthio or C₃-C₆-cycloalkyl-C₁-C₄-alkylamino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substituted phenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenyl-C₁-C₄-alkoxy, phenylthio, phenyl-C₁-C₄-alkylthio, phenylamino or phenyl-C₁-C₄-alkylamino, or

R⁴ and R⁵ together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and also

R⁶, R⁷ and R⁸ are identical or different and represent hydrogen, cyano, fluoro, chloro or bromo, or represent in each case optionally fluoro-, chloro-, bromo- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylsulphinyl and alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,

the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide being excluded by disclaimer.

The invention also relates preferably to sodium, potassium, magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium, di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which A, Q, R¹, R² and R³ have the meanings indicated above as preferred.

The invention relates in particular to compounds of the formula (I) in which

A represents a single bond, oxygen or the group N—R, in which R represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,

Q represents oxygen or sulphur,

R¹ represents hydrogen or formyl, or represents in each case optionally fluoro-, chloro-, bromo-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, acetyl, propionyl, butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, n-, i-, s- or t-butylsulphonyl, or represents in each case optionally fluoro-, chloro- or methyl-substituted cyclopropyl, cyclopropylcarbonyl or cyclopropylsulphonyl,

R² represents cyano, fluoro, chloro or bromo, or represents in each case optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy, butenyloxy, propinyloxy or butinyloxy and

R³ represents in each case optionally substituted heterocyclyl of the formulae below,

 in which

Q¹, Q² and Q³ each represent oxygen or sulphur, and

R⁴ represents hydrogen, hydroxyl or amino, or represents C₃-C₈-alkyli-deneamino, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy or butenyloxy, or represents dimethylamino or diethylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally fluoro-, chloro-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl,

R⁵ represents hydrogen, hydroxyl, mercapto, amino, fluoro, chloro or bromo, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted ethenyl, propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, or represents dimethylamino, diethylamino or dipropylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluoro-, chloro-, methyl-, trifluoromethyl-, methoxy- and/or methoxy-carbonyl substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or

R⁴ and R⁵ together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and also

R⁶, R⁷ and R⁸ are identical or different and represent hydrogen, cyano, fluoro, chloro or bromo, or represent in each case optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenytoxy, butenyloxy, propinyloxy, butinyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio, butenylthio, propinylthio, butinylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, or represent cyclopropyl,

the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide being excluded by disclaimer.

A very particularly preferred group of compounds according to the invention are the compounds of the formula (I), in which

A represents a single bond,

Q represents oxygen or sulphur,

R¹ represents methyl, ethyl, n- or i-propyl,

R² represents chloro or methyl- in each case in position 5 or 6- and

R³ represents optionally substituted triazolinyl of the formula below

 in which

Q¹ represents oxygen or sulphur, and

R⁴ represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents propenyl or a propinyl, or represents methoxy, ethoxy, n- or i-propoxy, or represents cyclopropyl, and

R⁵ represents hydrogen, chloro or bromo, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally fluoro and/or chloro-substituted propenyl or propinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, or represents propenyloxy or cyclopropyl.

The radical definitions listed above, whether general or listed in ranges of preference, apply not only to the end products of the formula (I) but also, correspondingly, to the starting materials and/or intermediates required in each case of the preparation. These radical definitions can be combined as desired with one another, thus including combinations between the preferred ranges indicated.

Using, for example, 2-fluoro-6-methoxy-benzenesulphonamide and 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazole-3-thione as starting materials, the course of reaction in the process (a) according to the invention can be illustrated by the following equation:

Using, for example, 2-ethoxy-6-methyl-phenylsulphonyl-isothiocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of reaction in the process (b) according to the invention can be illustrated by the following equation:

Using, for example, 2-methoxy-3-methyl-benzenesulphochloride, 5-ethylthio-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one and potassium cyanate as starting materials, the course of reaction in the process (c) according to the invention can be illustrated by the following equation:

Using, for example, 2-ethoxy-4-fluoro-benzenesulphochloride and 5-methyl-1,2,4-oxadiazole-3-carboxamide as starting materials, the course of reaction in the process (d) according to the invention can be illustrated by the following equation:

Using, for example, N-(2-chloro-6-propoxy-phenylsulphonyl)-O-methyl-urethane and 4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of reaction in the process (e) according to the invention can be illustrated by the following equation:

Using, for example, 5-chloro-4-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one and chlorosulphonylisocyanate and then 2-ethoxy-6-methyl-aniline as starting materials, the course of reaction in the process (f) according to the invention can be illustrated by the following equation:

A general definition of the aminosulphonyl compounds to be used as starting materials in the process (a) according to the invention for the preparation of compounds of the formula (I) is given by the formula (II). In the formula (II) A, R¹ and R² preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or, respectively, particularly preferable for A, R¹ and R².

The starting materials of the formula (II) are known and/or can be prepared by methods known per se (cf. EP 216504, DE 3208189, EP 44807, EP 23422).

Compounds not yet known from the literature, and which as novel substances are likewise a subject of the present application, are the sulphonamides of the general formula (IIa),

in which

A¹ represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethyl, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and

A² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The novel sulphonamides of the formula (IIa) are obtained if sulphonyl chlorides of the formula (VIa)

in which

A¹ and A² have the meanings given above

are reacted with ammonia, optionally in the presence of a diluent, for example water, at temperatures between 0° C. and 50° C. (cf. the Preparation Examples).

The starting materials of the formula (II) can in general be obtained also by reacting phenol derivatives of the formula (IIb)

in which

A and R² have the meanings given above

with alkylating agents of the formula (XI)

X—R¹  (XI)

 in which

R¹ has the meaning given above, and

X represents halogen or the group R¹—O—SO₂—O—,

optionally in the presence of an acid acceptor, for example potassium carbonate, and optionally in the presence of a diluent for example toluene, at temperatures between 10° C. and 150° C. (cf. the Preparation Examples).

The phenol derivatives of the formula (IIb) required as precursors are known and/or can be prepared by methods known per se (cf EP 44807, Metalloberfläche [Metal surface]—Angew. Elektrochernie 27 (1973), 217-227—cited in Chemn. Abstracts 79:86733; Preparation Examples).

The alkylating agents of the formula (XI) which are also required as precursors are known synthesis chemicals.

A general definition of the (thio)carboxylic acid derivatives also to be used as starting materials in the process (a) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (III). In the formula (III), Q and R³ preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or, respectively, particularly preferable for Q and R³; Z preferably represents fluorine, chlorine, bromine, C₁-C₄-alkoxy, phenoxy or benzyloxy, and in particular represents chlorine, methoxy, ethoxy or phenoxy.

The starting materials of the formula (III) are known and/or can be prepared by methods known per se (cf. EP 459244, EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266).

A general definition of the sulphonyl iso(thio)cyanate to be used as starting materials in the process (b) according to the invention for the preparation of the compounds of the formula (I) is given with the formula (IV). In the formula (IV), A, Q, R¹ and R² preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, Q, R¹ and R².

The starting materials of the formula (IV) are known and/or can be prepared by methods known per se (cf. EP 23422, EP 216504).

Compounds not yet known from the literature, and which as novel substances are likewise a subject of the present application, are the sulphonyl iso(thio)cyanates of the general formula (IVa)

in which

Q represents oxygen or sulphur,

A¹ represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethyl, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and

A² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The novel sulphonyl iso(thio)cyanates of the formula (IVa) are obtained if sulphonamides of the formula (IIa)—above—are reacted with phosgene or, respectively, thiophosgene, optionally in the presence of an alkyl isocyanate, for example butyl isocyanate, optionally in the presence of a reaction auxiliary, for example diazabicyclo[2.2.2]octane, and in the presence of a diluent, for example toluene, xylene or chlorobenzene, at temperatures between 80° C. and 150° C., and, after the end of the reaction, the volatile components are distilled off under reduced pressure.

A general definition of the heterocycles also to be used as starting materials in the processes (b), (c), (e) and (f) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (V). In the formula (V), R³ preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for R³.

The starting materials of the formula (V) are known and/or can be prepared by methods known per se (cf EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266).

A general definition of the chlorosulphonyl compounds to be used as starting materials in the processes (c) and (d) according to the invention for the preparation of compounds of the formula (I) is given by the formula (VI). In the formula (VI), A, R¹ and R² preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, R¹ and R².

The starting materials of the formula (VI) are known and/or can be prepared by methods known per se (cf. EP 511826, DE 3208189, EP23422).

Compounds not yet known from the literature, which as novel substances are likewise a subject of the present application, are the sulphonyl chlorides of the formula (VIa)

in which

A¹ represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethyl, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and

A² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The novel sulphonyl chlorides of the formula (VIa) are obtained if aniline derivatives of the formula (XII)

in which

A¹ and A² have the meanings given above

are reacted with an alkali metal nitrite, for example sodium nitrite, in the presence if hydrochloric acid at temperatures between −10° C. and +10° C., and the diazonium salt solution thus obtained is reacted with sulphur dioxide in the presence of a diluent, for example dichloromethane or 1,2-dichloro-ethane, and in the presence of a catalyst, for example copper(I) chloride, optionally in the presence of a further catalyst, for example dodecyltrimethylammonium bromide, at temperatures between −10° C. and +50° C. (cf. the Preparation Examples).

The aniline derivatives of the formula (XII) required as precursors are known and/or can be prepared by methods known per se (cf. EP 511826, U.S. Pat. No. 4,992,091, EP 185128, DE 2405479, Preparation Examples).

The abovementioned novel benzenesulphonic acid derivatives of the formulae (IIa), (IVa) and (VIa) can be defined comprehensively by the following formula (XIII):

in which

E represents —NH₂, —N═C═Q or —Cl, where

Q represents O or S, and also

A¹ represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethy, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and

A² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

A general definition of the (thio)carboxamides to be used as starting materials in the process (d) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (VIII). In the formula (VIII), Q and R³ preferably or in particular have that meaning which has already been indicated above, in connection with a description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for Q and R³.

The starting materials of the formula (VIII) are known and/or can be prepared by methods known per se (cf. EP 459244).

A general definition of the sulphonylamino(thio)carbonyl compounds to be used as starting materials in the process (e) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (IX). In the formula (IX), A, Q, R¹ and R² preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, Q, R¹ and R²; Z preferably represents fluoro, chloro, bromo, C₁-C₄-alkoxy, phenoxy or benzyloxy, and in particular represents chlorine, methoxy, ethoxy or phenoxy.

A general definition of the benzene derivatives to be used as starting materials in the process (f) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (X). In the formula (X), A, R¹ and R² preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, R¹ and R².

Starting materials of the formula (X) are known and/or can be prepared by methods known per se (cf. EP 511826, U.S. Pat. No. 4,992,091, EP 185128, DE 2405479, Preparation Examples).

The processes (a), (b), (c), (d), (e) and (f) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents in this context are virtually all inert organic solvents. These include, preferably, aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichlorobenzene; ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxanes; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone; esters such as methyl acetate and ethyl acetate; nitrites, for example acetonitrile and propionitrile; amides, for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.

As reaction auxiliaries and/or as acid acceptors in the processes (a), (b), (c), (d), (e) and (f) according to the invention it is possible to employ all acid-binding agents which can customarily be used for such reactions. Preferred among suitable examples are alkali metal hydroxides, for example sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides, for example calcium hydroxide, alkali metal carbonates and alcoholates, such as sodium carbonate and potassium carbonate, sodium tert-butylate and potassium tert-butylate, and also basic nitrogen compounds; such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2.2.2]-octane (DABCO).

The reaction temperatures in the processes (a), (b), (c), (d), (e) and (f) according to the invention can be varied within a relatively wide range. They are in general carried out at temperatures of between −20° C. and +150° C., preferably at temperatures between 0° C. and +100° C.

The processes (a), (b), (c), (d), (e) and (f) according to the invention are generally carried out under atmospheric pressure. However it is also possible to operate under increased or reduced pressure.

For carrying out processes (a), (b), (c), (d), (e) and (f) according to the invention, the starting materials required in each case are in general employed in approximately equimolar quantities. However, it is also possible to use one of the components employed in each case in a relatively large excess. The reactions are in general carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a number of hours at the particular temperature required. Working up in the case of the processes (a), (b), (c), (d), (e) and (f) according to the invention is in each case by customary methods (cf the Preparation Examples).

Salts of the compounds of the general formula (I) according to the invention can be prepared if desired. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in an appropriate solvent, for example methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding an appropriate base. The salts can then—if desired after prolonged stirring—be isolated by concentration or filtration with suction.

The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pasture-land, and for the selective combating of weeds in annual cultures.

The compounds of the formula (I) according to the invention are preferably suitable for combating monoctyledon and dicotyledon broad-leaved weeds, both pre-emergence and post-emergence. They exhibit strong herbicidal activity and a broad spectrum action when used on the soil and on above-ground parts of the plants.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.

In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.

As solid carriers there are suitable:

for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methyl cellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Possible components for the mixtures are known herbicides, for example anilides, for example diflufenican and propanil; arylcarboxylic acids, for example dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids, for example 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters, for example diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones, for example chloridazon and norflurazon; carbamates, for example chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides, for example alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines, for example oryzalin, pendimethalin and trifluralin; diphenyl ethers, for example acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas, for example chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines, for example alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, for example imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, for example bromoxynil, dichlobenil and ioxynil; oxyacetamides, for example mefenacet; sulphonyl-ureas, for example amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates, for example butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, for example atrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine; triazinones, for example hexazinone, metamitron and metribuzin; others, for example aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the following examples.

PREPARATION EXAMPLES Example 1

(Process (a))

A mixture of 2.5 g (10 mmol) of 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2.3 g (10 mmol) of 2-isopropoxy-6-methyl-benzenesulphonamide, 1.5 g (10 mmol) of diazabicyclo[5.4.0]undec-7-ene (DBU) and 50 ml of acetonitrile is stirred at 20° C. for 5 hours. It is then concentrated under a water pump vacuum and the residue is stirred with 50 ml of 1N hydrochloric acid, the mixture is filtered with suction, the filter product is stirred with diethyl ether and the mixture is again filtered with suction.

2.4 g (60% of theory) of 5-ethoxy-4-methyl-2-(2-isopropoxy-6-methyl-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 155° C.

Example 2

(Process (c))

A mixture of 1.7 g (10 mmol) of 4-methyl-5-propargylthio-2,4-dihydro-3H-1,2,4-triazol-3-one, 1.3 g (20 mmol) of sodium cyanate, 2.5 g (10 mmol) of 2-methyl-6-n-propoxy-benzenesulphochloride and 50 ml of acetonitrile is heated under reflux for 3 hours. It is then concentrated under a water pump vacuum, the residue is stirred with 1N hydrochloric acid and the mixture is subjected three times to extraction with 50 ml of methylene chloride each time. The combined organic extraction solutions are concentrated, the residue is digested with isopropanol and the crystalline product is isolated by filtration with suction.

2.2 g (52% of theory) of 4-methyl-5-propargylthio-2-(2-methyl-6-n-propoxy-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 151° C.

Example 3

(Process (d))

A mixture of 3.2 g (25 mmol) of 5-methyl-1,2,4-oxadiazole-3-carboxamide, 4.2g (75 mmol) of potassium hydroxide (powder) and 200 ml of dioxane is stirred at 60° C. for 30 minutes. It is then concentrated to about half its volume under a water pump vacuum, and a solution of 7 g (30 mmol) of 2-ethoxy-6-methyl-benzenesulphochloride in 10 ml of dioxane is added dropwise at about 20° C. The reaction mixture is then stirred at 20° C. for about 15 hours more. It is then concentrated under a water pump vacuum, the residue is stirred with 50 ml of 1N hydrochloric acid and the crystalline product is isolated by filtration with suction. 4.0 g (49% of theory) of N-(2-ethoxy-6-methyl-phenylsulphonyl)-5-methyl-1,2,4-oxadiazole-3-carboxamide are obtained of melting point 168° C.

Example 4

(Process (f))

1.7 g (12 mmol) of chlorosulphonyl isocyanate are added to a solution, cooled to 5° C., of 1.4 g (10 mmol) of 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 50 ml of methylene chloride, and then a solution of 1.5 g (10 mmol) of 2-ethoxy-6-methyl-aniline and 1.0 g (10 mmol) of triethylamine in 10 ml of methylene chloride is added dropwise, likewise at 5° C. The reaction mixture is then stirred at about 20° C. for 15 hours. Subsequently, 100 ml of 1N hydrochloric acid are added. After a thorough stirring, the organic phase is separated off, dried over sodium sulphate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is digested with isopropanol and the crystalline product is isolated by filtration with suction.

1.8 g (45% of theory) of 5-ethoxy-4-methyl-2-(2-ethoxy-6-methyl-phenyl-aminosulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 147° C.

In analogy to Example 1 to 4 and in accordance with the general description of the preparation processes according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in Table 1 below (showing Examples Nos. 5-965), as well as the compounds of the formula (IA) listed in Table IA thereafter (showing Examples Nos. 966-1637):

TABLE 1 Examples of the compounds of the formula (I) Ex. No. A Q R¹ (position-) R² R³ Melting point (° C.)  5 — O n-C₃H₇ (6-) CH₃

117  6 — O C₂H₅ (6-) Cl

156  7 — O C₂H₅ (6-) CH₃

110  8 — O C₂H₅ (6-) CH₃

141  9 — O C₂H₅ (6-) CH₃

162  10 — O n-C₃H₇ (6-) CH₃

126  11 — O n-C₃H₇ (6-) CH₃

150  12 — O n-C₃H₇ (6-) CH₃

129  13 — O CH₃ (6-) CH₃

153  14 — O CH₃ (6-) CH₃

167  15 — O CH₃ (6-) CH₃

167  16 — O i-C₃H₇ (6-) CH₃

125  17 — O i-C₃H₇ (6-) CH₃

131  18 — O C₂H₅ (5-) CH₃

222  19 — O C₂H₅ (5-) CH₃

139  20 — O C₂H₅ (4-) CH₃

189  21 — O C₂H₅ (5-) CH₃

131  22 — O —C₂H₄—OC₂H₅ (6-) CH₃

118  23 — O —CH₂CH₂Cl (6-) CH₃

137  24 — O —CH₂CH₂Cl (6-) CH₃

149  25 — O i-C₃H₇ (5-) CH₃

125  26 — O i-C₃H₇ (5-) CH₃

140  27 — O n-C₃H₇ (5-) CH₃

119  28 — O n-C₃H₇ (5-) CH₃

134  29 — O n-C₃H₇ (5-) CH₃

110  30 — O C₂H₅ (6-) CH₃

108  31 — O C₂H₅ (6-) CH₃

173  32 — O C₂H₅ (6-) CH₃

119  33 — O C₂H₅ (6-) CH₃

121  34 — O C₂H₅ (6-) CH₃

109  35 — O C₂H₅ (6-) CH₃

111  36 — O n-C₃H₇ (6-) CH₃

 91  37 — O n-C₃H₇ (6-) CH₃

130  38 — O n-C₃H₇ (6-) CH₃

126  39 — O n-C₃H₇ (6-) CH₃

101  40 — O n-C₃H₇ (6-) CH₃

152  41 — O n-C₃H₇ (6-) CH₃

100  42 — O n-C₃H₇ (6-) CH₃

120  43 — O n-C₃H₇ (6-) CH₃

117  44 — O n-C₃H₇ (6-) CH₃

126  45 — O n-C₃H₇ (6-) CH₃

113  46 — O i-C₃H₇ (6-) CH₃

130  47 — O i-C₃H₇ (6-) CH₃

139  48 — O i-C₃H₇ (6-) CH₃

121  49 — O i-C₃H₇ (6-) CH₃

119  50 — O i-C₃H₇ (6-) CH₃

128  51 — O i-C₃H₇ (6-) CH₃

134  52 — O i-C₃H₇ (6-) CH₃

130  53 — O i-C₃H₇ (6-) CH₃

117  54 — O i-C₃H₇ (6-) CH₃

134  55 — O i-C₃H₇ (6-) CH₃

141  56 — O i-C₃H₇ (6-) CH₃

132  57 — O i-C₃H₇ (6-) CH₃

166  58 — O i-C₃H₇ (6-) CH₃

118  59 — O i-C₃H₇ (6-) CH₃

150  60 — O i-C₃H₇ (6-) CH₃

144  61 — O i-C₃H₇ (6-) CH₃

170  62 — O i-C₃H₇ (6-) CH₃

120  63 — O n-C₃H₇ (6-) CH₃

124  64 — O n-C₃H₇ (6-) CH₃

125  65 — O n-C₃H₇ (6-) CH₃

116  66 — O n-C₃H₇ (6-) CH₃

152  67 — O n-C₃H₇ (6-) CH₃

143  68 — O C₂H₅ (6-) CH₃

160  69 — O C₂H₅ (6-) CH₃

133  70 — O C₂H₅ (6-) CH₃

 97  71 — O C₂H₅ (6-) CH₃

 96  72 — O C₂H₅ (6-) CH₃

156  73 — O C₂H₅ (6-) CH₃

145  74 — O C₂H₅ (6-) CH₃

120  75 — O C₂H₅ (6-) CH₃

125  76 — O C₂H₅ (6-) CH₃

140  77 — O H (6-) CH₃

 88  78 — O C₂H₅ (5-) CH₃

130  79 — O n-C₃H₇ (6-) CH₃

141  80 — O n-C₃H₇ (6-) CH₃

 98  81 — O n-C₃H₇ (6-) CH₃

141  82 — O n-C₃H₇ (6-) CH₃

101  83 — O n-C₃H₇ (6-) CH₃

136  84 — O n-C₃H₇ (6-) CH₃

 96  85 — O n-C₃H₇ (6-) CH₃

 90  86 — O n-C₃H₇ (6-) CH₃

136  87 — O C₂H₅ (6-) CH₃

122  88 — O C₂H₅ (6-) CH₃

154  89 — O i-C₃H₇ (6-) CH₃

139  90 — O C₂H₅ (6-) CH₃

142  91 — O C₂H₅ (6-) CH₃

153  92 — O C₂H₅ (6-) CH₃

145  93 — O C₂H₅ (6-) CH₃

132  94 — O C₂H₅ (6-) CH₃

141  95 — O C₂H₅ (6-) CH₃

130  96 — O CH₃ (5-) CH₃

156  97 — O CH₃ (5-) CH₃

177  98 — O CH₃ (4-) CH₃

115  99 — O CH₃ (4-) CH₃

166 100 — O CH₃ (3-) CH₃

162 101 — O CH₃ (3-) CH₃

143 102 — O CH₃ (3-) CH₃

165 103 — O CHF₂ (5-) CH₃

176 104 — O CHF₂ (5-) CH₃

119 105 — O CHF₂ (5-) CH₃

126 106 — O CHF₂ (5-) CH₃

151 107 — O CHF₂ (5-) CH₃

188 108 — O CHF₂ (5-) CH₃

137 109 — O CHF₂ (5-) CH₃

117 110 — O CHF₂ (5-) CH₃

155 111 — O CHF₂ (4-) CH₃

152 112 — O CHF₂ (4-) CH₃

176 113 — O CHF₂ (4-) CH₃

108 114 — O CHF₂ (6-) CH₃

163 115 — O CHF₂ (6-) CH₃

136 116 — O CHF₂ (6-) CH₃

118 117 — O CHF₂ (6-) CH₃

104 118 — O CHF₂ (5-) CH₃

 98 119 — O CHF₂ (6-) CH₃

128 120 — O CHF₂ (6-) CH₃

165 121 — O CHF₂ (6-) CH₃

155 122 — O CHF₂ (6-) CH₃

105 123 — O CHF₂ (6-) CH₃

 81 124 — O CHF₂ (6-) CH₃

174 125 — O CHF₂ (5-) CH₃

150 126 — O CHF₂ (6-) CH₃

124 127 — O CHF₂ (6-) CH₃

200 128 — S n-C₃H₇ (6-) CH₃

160 129 — S n-C₃H₇ (6-) CH₃

148 130 — S C₂H₅ (6-) CH₃

141 131 — S C₂H₅ (6-) CH₃

125 132 — S C₂H₅ (6-) CH₃

158 133 — S i-C₃H₇ (6-) CH₃

155 134 — S n-C₃H₇ (6-) CH₃

153 135 — S n-C₃H₇ (6-) CH₃

131 136 — S n-C₃H₇ (6-) CH₃

120 137 — O C₂H₅ (6-) Cl

149 138 — O C₂H₅ (6-) Cl

 99 139 — O CH₃ (6-) Cl

176 140 — O CH₃ (6-) Cl

192 141 — O C₂H₅ (6-) Cl

144 142 — O CH₃ (6-) Cl

114 143 — O C₂H₅ (6-) Cl

144 144 — O CH₃ (6-) Cl

157 145 — O C₂H₅ (6-) Cl

142 146 — O CH₃ (6-) Cl

191 147 — O C₂H₅ (6-) Cl

116 148 — O CH₃ (6-) Cl

205 149 — O CH₃ (6-) Cl

147 150 — O C₂H₅ (6-) Cl

117 151 — O CH₃ (6-) Cl

149 152 — O CH₃ (6-) Cl

176 153 — O CH₃ (6-) Cl

150 154 — O CH₃ (6-) Cl

146 155 — O CH₃ (6-) Cl

191 156 — O CH₃ (6-) Cl

127 157 — O CH₃ (6-) Cl

174 158 — O n-C₃H₇ (6-) Cl

117 159 — O n-C₃H₇ (6-) Cl

134 160 — O n-C₃H₇ (6-) Cl

115 161 — O n-C₃H₇ (6-) Cl

137 162 — O n-C₃H₇ (6-) Cl

125 163 — O n-C₃H₇ (6-) Cl

119 164 — O H (6-) Cl

147 165 — O n-C₃H₇ (6-) Cl

148 166 — O i-C₃H₇ (6-) Cl

143 167 — O i-C₃H₇ (6-) Cl

122 168 — O CH₃ (6-) Cl

165 169 — O n-C₃H₇ (5-) Cl

154 170 — O n-C₃H₇ (5-) Cl

136 171 — O n-C₃H₇ (5-) Cl

128 172 — O CH₃ (6-) Cl

143 173 — O i-C₃H₇ (6-) Cl

136 174 — O i-C₃H₇ (6-) Cl

121 175 — O i-C₃H₇ (6-) Cl

158 176 — O i-C₃H₇ (6-) Cl

141 177 — O i-C₃H₇ (6-) Cl

127 178 — O i-C₃H₇ (6-) Cl

143 179 — O i-C₃H₇ (6-) Cl

129 180 — O i-C₃H₇ (6-) Cl

 95 181 — O n-C₃H₇ (6-) CH₃

 74 182 — O n-C₃H₇ (6-) CH₃

114 183 — O n-C₃H₇ (6-) CH₃

140 184 — O n-C₃H₇ (6-) CH₃

159 185 — O n-C₃H₇ (6-) CH₃

107 186 — O n-C₃H₇ (6-) CH₃

132 187 — O n-C₃H₇ (6-) CH₃

132 188 — O n-C₃H₇ (6-) CH₃

110 189 — O CH₃ (6-) CH₃

159 190 — O n-C₃H₇ (6-) CH₃

138 191 — O n-C₃H₇ (6-) CH₃

147 192 — O n-C₃H₇ (6-) CH₃

114 193 — O n-C₃H₇ (6-) CH₃

125 194 — O n-C₃H₇ (6-) CH₃

126 195 — O n-C₃H₇ (6-) CH₃

151 196 — O n-C₃H₇ (6-) CH₃

121 197 — O n-C₃H₇ (6-) CH₃

147 198 NH O C₂H₅ (6-) CH₃

135 199 — O i-C₃H₇ (6-) CH₃

263 (Sodium salt) 200 — O C₂H₅ (6-) CH₃

119 201 — O C₂H₅ (6-) CH₃

146 202 — O C₂H₅ (6-) CH₃

128 203 — O C₂H₅ (6-) CH₃

186 204 — O C₂H₅ (6-) CH₃

239 205 — O C₂H₅ (6-) CH₃

152 206 — O C₂H₅ (6-) CH₃

155 207 — O C₂H₅ (6-) CH₃

145 (Na salt) 208 — O i-C₃H₇ (6-) CH₃

209 (Na salt) 209 — O C₂H₅ (6-) CH₃

147 (Na salt) 210 — O C₂H₅ (6-) CH₃

140 211 — O C₂H₅ (6-) CH₃

118 212 — O C₂H₅ (6-) CH₃

156 213 — O C₂H₅ (6-) CH₃

110 214 — O C₂H₅ (6-) CH₃

133 215 — O i-C₃H₇ (6-) CH₃

138 216 — O i-C₃H₇ (6-) CH₃

154 217 — O i-C₃H₇ (6-) CH₃

149 218 — O i-C₃H₇ (6-) CH₃

112 219 — O i-C₃H₇ (6-) CH₃

162 220 — O i-C₃H₇ (6-) CH₃

 99 221 — O i-C₃H₇ (6-) CH₃

146 222 — O C₂H₅ (6-) CH₃

134 223 — O CH₃ (6-) CH₃

199 224 — O CH₃ (6-) CH₃

176 225 — O CH₃ (6-) CH₃

145 226 — O i-C₃H₇ (6-) CH₃

133 227 NH O n-C₃H₇ (5-) CH₃

127 228 — O i-C₃H₇ (6-) CH₃

144 229 — O i-C₃H₇ (6-) CH₃

141 230 — O i-C₃H₇ (6-) CH₃

152 231 — O i-C₃H₇ (6-) CH₃

132 232 — O i-C₃H₇ (6-) CH₃

147 233 — O i-C₃H₇ (6-) CH₃

163 234 — O i-C₃H₇ (6-) CH₃

102 235 — O C₂H₅ (6-) CH₃

121 236 — O C₂H₅ (6-) CH₃

113 237 — O C₂H₅ (6-) CH₃

145 238 — O C₂H₅ (6-) CH₃

137 239 — O C₂H₅ (6-) CH₃

172 240 — O C₂H₅ (6-) CH₃

148 241 — O C₂H₅ (6-) CH₃

157 242 — O C₂H₅ (6-) CH₃

186 243 NH O CH₃ (6-) OCH₃

170 244 — O CHF₂ (5-) CH₃

245 — S i-C₃H₇ (6-) CH₃

160 246 — O CH₃ (6-) CF₃

205 247 — S CH₃ (6-) CF₃

 92 248 — S CH₃ (6-) CF₃

154 249 — S CH₃ (6-) CF₃

157 250 — O C₂H₅ (6-) CF₃

176 251 — O n-C₃H₇-n (6-) CF₃

166 252 — O i-C₃H₇ (6-) CF₃

190 253 — O CH₃ (6-) CF₃

203 254 — O CH₃ (6-) CF₃

156 255 — O CH₃ (6-) CF₃

170 256 — O CH₃ (6-) CF₃

198 257 — O CH₃ (6-) CF₃

213 258 — O CH₃ (6-) CF₃

152 259 — O CH₃ (6-) CF₃

187 260 — O CH₃ (6-) CF₃

210 261 — O CH₃ (6-) CF₃

172 262 — O CH₃ (6-) CF₃

145 263 — O CH₃ (6-) CF₃

136 264 — O CH₃ (6-) CF₃

153 265 — O CH₃ (6-) CF₃

136 266 — O CH₃ (6-) CF₃

210 267 — O CH₃ (6-) CF₃

147 268 — O CH₃ (6-) CF₃

169 269 — O CH₃ (6-) CF₃

215 270 — O CH₃ (6-) CF₃

138 271 — O CH₃ (6-) CF₃

182 272 — S C₂H₅ (6-) CF₃

112 273 — S C₂H₅ (6-) CF₃

167 274 — S C₂H₅ (6-) CF₃

152 275 — S n-C₃H₇ (6-) CF₃

119 276 — S n-C₃H₇ (6-) CF₃

157 277 — S n-C₃H₇ (6-) CF₃

154 278 — S i-C₃H₇ (6-) CF₃

137 279 — S i-C₃H₇ (6-) CF₃

167 280 — S i-C₃H₇ (6-) CF₃

137 281 — O C₂H₅ (6-) CF₃

154 282 — O C₂H₅ (6-) CF₃

160 283 — O C₂H₅ (6-) CF₃

139 284 — O C₂H₅ (6-) CF₃

134 285 — O C₂H₅ (6-) CF₃

142 286 — O C₂H₅ (6-) CF₃

120 287 — O n-C₃H₇ (6-) CF₃

130 288 — O n-C₃H₇ (6-) CF₃

127 289 — O n-C₃H₇ (6-) CF₃

116 290 — O n-C₃H₇ (6-) CF₃

126 291 — O n-C₃H₇ (6-) CF₃

113 292 — O i-C₃H₇ (6-) CF₃

151 293 — O i-C₃H₇ (6-) CF₃

157 294 — O i-C₃H₇ (6-) CF₃

171 295 — O i-C₃H₇ (6-) CF₃

137 296 — O i-C₃H₇ (6-) CF₃

125 297 — O n-C₃H₇ (6-) CF₃

109 298 — O n-C₃H₇ (6-) CF₃

138 299 — O i-C₃H₇ (6-) CF₃

130 300 — O C₂H₅ (6-) CF₃

165 301 — O i-C₃H₇ (6-) CF₃

148 302 — O i-C₃H₇ (6-) CF₃

147 303 — O i-C₃H₇ (6-) CF₃

172 304 — O i-C₃H₇ (6-) CF₃

147 305 — O i-C₃H₇ (6-) CF₃

136 306 — O C₂H₅ (6-) CF₃

124 307 — O C₂H₅ (6-) CF₃

 98 308 — O C₂H₅ (6-) CF₃

125 309 — O C₂H₅ (6-) CF₃

179 310 — O C₂H₅ (6-) CF₃

153 311 — O C₂H₅ (6-) CF₃

171 312 — O n-C₃H₇ (6-) CF₃

113 313 — O n-C₃H₇ (6-) CF₃

138 314 — O n-C₃H₇ (6-) CF₃

110 315 — O n-C₃H₇ (6-) CF₃

134 316 — O i-C₃H₇ (6-) CF₃

167 317 — O i-C₃H₇ (6-) CF₃

120 318 — O i-C₃H₇ (6-) CF₃

117 319 — O i-C₃H₇ (6-) CF₃

160 320 — O i-C₃H₇ (6-) CF₃

154 321 — O i-C₃H₇ (6-) CF₃

159 322 — O n-C₃H₇ (6-) CF₃

141 323 — O i-C₃H₇ (6-) CF₃

146 324 — O i-C₃H₇ (6-) CF₃

134 325 — O i-C₃H₇ (6-) CF₃

168 326 — O CH₃ (6-) C₃H₇-n

158 327 — O CH₃ (6-) C₃H₇-n

172 328 — O CH₃ (6-) C₃H₇-n

147 329 — O C₂H₅ (6-) CF₃

 66 330 — O C₂H₅ (6-) CH₃

134 331 — O C₂H₅ (6-) CH₃

149 332 — O n-C₃H₇ (6-) CH₃

114 333 — O H (6-) Cl

102 334 — O H (6-) Cl

143 335 — O

(6-) Cl

130 336 — O —CH₂C₆H₅ (6-) Cl

143 337 — O —CH₂C₆H₅ (6-) Cl

 99 338 — O —CH₂C≡CH (6-) Cl

161 339 — O n-C₃H₇ (6-) CH₃

133 340 — O H (6-) CH₃

100 341 — O H (6-) CH₃

147 342 — O —CH₂C₆H₅ (6-) CH₃

157 343 — O

(6-) CH₃

150 344 — O —CH₂C≡CH (6-) CH₃

172 345 — O i-C₃H₇ (6-) CH₃

263 (Na salt) 346 — O C₂H₅ (6-) CH₃

136 347 — O i-C₃H₇ (6-) CH₃

113 348 — O i-C₃H₇ (6-) CH₃

175 349 — O i-C₃H₇ (6-) CH₃

135 350 — O i-C₃H₇ (6-) CH₃

 78 351 — O i-C₃H₇ (6-) CH₃

125 352 — O i-C₃H₇ (6-) CH₃

140 353 — O CH₃ (6-) CH₃

161 354 — O CH₃ (6-) CH₃

142 355 — O CH₃ (6-) CH₃

124 356 — O CH₃ (6-) CH₃

153 357 — O CH₃ (6-) CH₃

170 358 — O CH₃ (6-) CH₃

116 359 — O CH₃ (6-) CH₃

120 360 — O CH₃ (5-) Cl

172 361 — O CH₃ (5-) Cl

175 362 — O CH₃ (5-) Cl

192 363 — O CH₃ (5-) Cl

195 364 — O CH₃ (5-) Cl

174 365 — O CH₃ (5-) Cl

160 366 — O CH₃ (5-) Cl

214 367 — O CH₃ (5-) Cl

185 368 — O CH₃ (5-) Cl

191 369 NH O CH₃ (6-) CH₃

161 370 NH O i-C₃H₇ (6-) CH₃

132 371 NH O CH₃ (6-) OCH₃

151 372 NH O CH₃ (6-) CH₃

161 373 NH O i-C₃H₇ (6-) CH₃

128 374 NH O CH₃ (6-) CH₃

140 375 — S i-C₃H₇ (6-) CH₃

108 376 — O CHF₂ (4-) CH₃

131 377 — O CH₃ (6-) CF₃

187 378 — O CH₃ (6-) CF₃

154 379 — O CH₃ (6-) C₂H₅

179 380 — O CH₃ (6-) C₂H₅

178 381 — O CH₃ (6-) C₂H₅

167 382 — O C₂H₅ (6-) C₂H₅

135 383 — O C₂H₅ (6-) C₂H₅

146 384 — O C₂H₅ (6-) C₂H₅

174 385 — O CH₃ (6-) C₂H₅

130 386 — O CH₃ (6-) C₂H₅

195 387 — O CH₃ (6-) C₂H₅

183 388 — O C₂H₅ (6-) C₃H₇-n

135 389 — O C₂H₅ (6-) C₃H₇-n

149 390 — O CH₃ (6-) C₃H₇-n

193 391 — O CH₃ (6-) C₃H₇-n

125 392 — O CH₃ (6-) C₃H₇-n

182 393 — O C₂H₅ (6-) C₃H₇-n

120 394 — O C₂H₅ (6-) C₃H₇-n

158 395 — O i-C₃H₇ (6-) CH₃

180 396 — O n-C₄H₉ (6-) CH₃

132 397 — O n-C₄H₉ (6-) CH₃

143 398 — O n-C₄H₉ (6-) CH₃

106 399 — O n-C₄H₉ (6-) CH₃

 98 400 — O n-C₄H₉ (6-) CH₃

140 401 — O CH₃ (6-) CH₃

147 402 — O CH₃ (6-) CH₃

123 403 — O CH₃ (6-) CH₃

185 404 — O CH₃ (6-) CH₃

154 405 NH O i-C₃H₇ (6-) CH₃

150 406 — O C₂H₅ (6-) C₂H₅

135 407 — O C₂H₅ (6-) C₂H₅

134 408 — O C₂H₅ (6-) C₂H₅

178 409 — O C₃H₇-i (6-) C₂H₅

109 410 — O C₃H₇-i (6-) C₂H₅

125 411 — O C₃H₇-i (6-) C₂H₅

161 412 — O C₃H₇-i (6-) C₂H₅

114 413 — O C₃H₇-i (6-) C₂H₅

142 414 — O C₃H₇-i (6-) C₂H₅

124 415 — O CH₃ (6-) C₂H₅

175 (Na salt) 416 — O C₂H₅ (6-) C₃H₇-n

126 417 — O C₂H₅ (6-) C₃H₇-n

121 418 — O CH₃ (6-) C₃H₇-n

109 419 — O CH₃ (6-) C₃H₇-n

145 420 — O CH₃ (6-) C₃H₇-n

126 421 — O CH₃ (6-) C₃H₇-n

130 422 — O CH₃ (6-) C₃H₇-n

155 423 — O CH₃ (6-) C₃H₇-n

133 424 — O CH₃ (6-) C₃H₇-n

145 425 — O —SO₂CH₃ (6-) CH₃

 95 426 — O —SO₂CH₃ (6-) CH₃

153 427 — O C₄H₉-n (6-) CH₃

154 428 — O —CH₂C≡CH (6-) CH₃

167 429 — O —CH₂C≡CH (6-) CH₃

170 430 — O —CH₂C≡CH (6-) CH₃

153 431 — O C₄H₉-i (6-) CH₃

123 432 — O C₄H₉-i (6-) CH₃

145 433 — O C₄H₉-i (6-) CH₃

143 434 — O C₃H₇-i (6-) CH₃

138 435 — O C₃H₇-i (6-) CH₃

161 436 — O C₃H₇-i (6-) CH₃

128 437 — O C₃H₇-i (6-) CH₃

177 438 — O C₃H₇-i (6-) CH₃

165 439 — O CH₃ (6-) CH₃

157 440 — O CH₃ (6-) CH₃

168 441 — O CH₃ (6-) CH₃

164 442 — O CH₃ (6-) CH₃

125 443 — O CH₃ (6-) CH₃

162 444 — O CH₃ (6-) OCH₃

154 445 — S CH₃ (4-) C₃H₇-i

116 446 — S CH₃ (4-) C₃H₇-i

110 447 — S CH₃ (4-) C₃H₇-i

134 448 — O CH₃ (4-) C₃H₇-i

152 449 — O CH₃ (4-) C₃H₇-i

159 450 — O CH₃ (4-) C₃H₇-i

150 451 — O C₂H₅ (6-) OCH₃

107 452 — O C₂H₅ (6-) OCH₃

104 453 — O C₂H₅ (6-) OCH₃

100 454 — S C₂H₅ (6-) OCH₃

103 455 — S C₂H₅ (6-) OCH₃

 95 456 — S C₂H₅ (6-) OCH₃

105 457 — O C₂H₅ (6-) OC₂H₅

130 458 — O C₂H₅ (6-) OC₂H₅

100 459 — O C₃H₇-i (6-) OC₃H₇-i

114 460 — O C₃H₇-i (6-) OC₃H₇-i

125 461 — S C₃H₇-i (6-) OC₃H₇-i

143 462 — O C₂H₅ (6-) OC₂H₅

120 463 — O —CF₂CHFCl (6-) CH₃

124 464 — O —CF₂CHFCl (6-) CH₃

115 465 — O —CF₂CHFCl (6-) CH₃

150 466 — O CH₃ (3-) CH₃

178 467 — O CH₃ (3-) Cl

188 468 — O C₂H₅ (3-) Cl

159 469 — O CH₃ (3-) F

176 470 — O C₂H₅ (6-) CF₃

124 471 — O C₂H₅ (6-) CF₃

 34 472 — O C₂H₅ (6-) CF₃

 68 473 — O C₃H₇-i (6-) CF₃

 41 474 — O C₂H₅ (6-) CF₃

127 475 — O H (6-) CF₃

125 476 — S C₂H₅ (6-) CH₃

214 (Na salt) 477 NH O C₂H₅ (6-) CH₃

128 478 NH O C₂H₅ (6-) CH₃

148 479 NH O C₃H₇-n (6-) CH₃

127 480 NH O C₃H₇-n (6-) CH₃

 57 481 NH O C₂H₅ (6-) CH₃

125 482 NH O C₃H₇-n (6-) CH₃

115 483 NH O C₃H₇-n (6-) CH₃

151 484 NH O C₂H₅ (5-) CH₃

132 485 NH O C₂H₅ (5-) CH₃

106 486 NH O C₂H₅ (5-) CH₃

163 487 NH O C₂H₅ (5-) CH₃

137 488 — O C₂H₅ (6-) C₃H₇-i

166 489 — O C₂H₅ (6-) C₃H₇-i

169 490 — O C₂H₅ (6-) C₃H₇-i

130 491 NH O

(6-) CH₃

148 492 NH O

(6-) CH₃

138 493 NH O

(6-) CH₃

147 494 — O

(6-) CH₃

124 495 — O

(6-) CH₃

152 496 — O

(6-) CH₃

141 497 — O

(6-) CH₃

127 498 — O

(6-) CH₃

144 499 — O

(6-) CH₃

107 500 — O C₃H₇-n (6-) CH₃

265 (Na salt) 501 — O C₂H₅ (6-) CH₃

269 (Na salt) 502 — O C₃H₇-i (6-) CH₃

237 (Na salt) 503 — O

(6-) CH₃

 73 504 — O C₃H₇-i (6-) CH₃

220 (Na salt) 505 — O C₃H₇-i (6-) CH₃

140 506 — O C₄H₉-s (6-) CH₃

120 507 — O C₄H₉-s (6-) CH₃

117 508 — O C₄H₉-s (6-) CH₃

128 509 — O C₄H₉-s (6-) CH₃

232 510 — O C₄H₉-s (6-) CH₃

268 511 — O C₄H₉-s (6-) CH₃

130 512 — O C₄H₉-s (6-) CH₃

137 513 — O C₄H₉-s (6-) CH₃

145 514 — O C₄H₉-s (6-) CH₃

164 515 — O C₄H₉-s (6-) CH₃

 89 516 — O C₄H₉-s (6-) CH₃

 86 517 — O C₄H₉-s (6-) CH₃

 98 518 — O C₄H₉-s (6-) CH₃

122 519 — O C₄H₉-s (6-) CH₃

135 520 — O C₂H₅ (6-) CH₃

142 521 — O CH₃ (6-) CH₃

157 522 — O C₃H₇-n (6-) CH₃

126 523 — O C₄H₉-s (6-) CH₃

140 524 — O C₂H₅ (6-) CH₃

164 525 — O CH₃ (6-) CH₃

166 526 — O C₃H₇-n (6-) CH₃

145 527 — O CH₃ (6-) CH₃

239 (Na salt) 528 — O C₃H₇-n (6-) CH₃

206 (Na salt) 529 — O C₂H₅ (6-) CH₃

211 (Na salt) 530 — O CH₃ (6-) C₃H₇-i

166 531 — O CH₃ (6-) C₃H₇-i

178 532 — O C₃H₇-i (6-) C₃H₇-i

131 533 — O C₃H₇-i (6-) C₃H₇-i

130 534 — O C₃H₇-i (6-) C₃H₇-i

133 535 — O C₃H₇-i (6-) C₃H₇-i

116 536 — O CH₃ (6-) C₃H₇-i

192 537 — O CH₃ (6-) C₃H₇-i

200 538 — O CH₃ (6-) C₃H₇-i

200 539 — O CH₃ (6-) C₃H₇-i

105 540 — O CH₃ (6-) C₃H₇-i

154 541 — O CH₃ (6-) C₃H₇-i

152 542 — O C₃H₇-n (6-) C₃H₇-i

132 543 — O C₃H₇-n (6-) C₃H₇-i

129 544 — O C₃H₇-n (6-) C₃H₇-i

179 545 — O CH₃ (6-) C₃H₇-i

174 (Na salt) 546 — O C₃H₇-n (6-) C₃H₇-i

158 (Na salt) 547 — O C₂H₅ (6-) C₃H₇-i

200 548 — O C₂H₅ (6-) C₃H₇-i

147 549 — O C₂H₅ (6-) C₃H₇-i

149 550 — O C₂H₅ (6-) C₃H₇-i

136 551 — O C₂H₅ (6-) C₃H₇-i

134 552 — O C₃H₇-i (6-) C₃H₇-i

175 553 — O C₃H₇-i (6-) C₃H₇-i

147 554 — O C₃H₇-i (6-) C₃H₇-i

167 555 — O C₃H₇-i (6-) C₃H₇-i

173 556 — O C₃H₇-i (6-) CH₃

188 557 NH O CH₃ (6-) CH₃

181 558 NH O C₃H₇-i (6-) CH₃

136 559 — O CH₃ (6-) CH₃

241 (Na salt) 560 NH O C₃H₇-n (6-) CH₃

129 561 — O C₃H₇-i (6-) OCH₃

 94 562 — O C₃H₇-i (6-) OCH₃

 80 563 — O C₃H₇-i (6-) OC₂H₅

 68 564 — O C₃H₇-i (6-) OC₂H₅

 91 565 — O C₃H₇-n (6-) OCH₃

123 566 — O C₃H₇-n (6-) OCH₃

104 567 — O C₃H₇-n (6-) OCH₃

 90 568 — S C₃H₇-n (6-) OCH₃

107 569 — O C₃H₇-n (6-) OCH₃

 70 570 — O C₂H₅ (6-) OC₂H₅

132 571 — S CH₃ (6-) OCH₃

150 572 — O C₂H₅ (6-) OCH₃

127 573 — O C₃H₇-i (6-) OC₃H₇-i

110 574 — S C₃H₇-n (6-) OC₃H₇-n

130 575 — S C₃H₇-n (6-) OC₃H₇-n

135 576 — S C₃H₇-n (6-) OC₃H₇-n

199 (Na salt) 577 — O C₂H₅ (6-) OC₂H₅

173 578 — O C₂H₅ (6-) OCH₃

168 579 — O C₃H₇-n (6-) OC₃H₇-n

125 580 — O C₃H₇-n (6-) OC₂H₅

140 581 — O C₃H₇-n (6-) OCH₃

115 582 — S C₃H₇-n (6-) OCH₃

111 583 — S C₃H₇-n (6-) OCH₃

138 584 — O C₃H₇-i (6-) OCH₃

127 585 — O C₃H₇-i (6-) OC₂H₅

142 586 — O C₃H₇-i (6-) OC₂H₅

143 587 — O C₂H₅ (6-) OCH₃

104 588 — O C₂H₅ (6-) OCH₃

118 589 — O C₂H₅ (6-) OCH₃

 70 590 — O C₂H₅ (6-) OCH₃

110 591 — O C₂H₅ (6-) OCH₃

156 592 — O C₃H₇-n (6-) OCH₃

140 593 — O C₃H₇-n (6-) OCH₃

148 594 — O C₃H₇-n (6-) OCH₃

145 595 — O C₂H₅ (6-) OCH₃

120 596 — O C₂H₅ (6-) OCH₃

100 597 — O C₂H₅ (6-) OCH₃

130 598 — O C₂H₅ (6-) OCH₃

103 599 — O C₂H₅ (6-) OCH₃

104 600 — O C₃H₇-n (6-) OCH₃

185 601 — O C₃H₇-n (6-) OCH₃

100 602 — O C₃H₇-n (6-) OCH₃

138 603 — O C₃H₇-n (6-) OCH₃

106 604 — O C₃H₇-n (6-) OCH₃

112 605 — O C₃H₇-n (6-) OCH₃

140 606 — O C₃H₇-n (6-) OCH₃

160 607 — O C₃H₇-n (6-) OCH₃

180 608 — O C₃H₇-n (6-) OCH₃

142 609 — O C₃H₇-n (6-) OCH₃

158 610 — O C₃H₇-n (6-) OCH₃

134 611 — O C₃H₇-i (6-) OCH₃

140 612 — O C₃H₇-i (6-) OCH₃

142 613 — O C₃H₇-i (6-) OCH₃

148 614 — O C₃H₇-i (6-) OCH₃

146 615 — O C₃H₇-i (6-) OCH₃

104 616 — O C₂H₅ (6-) OC₂H₅

123 617 — O C₃H₇-n (6-) OC₃H₇-n

123 618 — O C₃H₇-n (6-) OC₃H₇-n

 82 619 — O C₃H₇-n (6-) OC₃H₇-n

 81 620 — S C₃H₇-n (6-) OC₃H₇-n

 88 621 — S C₂H₅ (6-) OCH₃

145 622 — S C₂H₅ (6-) OC₂H₅

147 623 — S C₃H₇-n (6-) OCH₃

205 624 — S C₃H₇-n (6-) OC₂H₅

202 625 — S C₃H₇-i (6-) OC₃H₇-i

152 626 — S C₂H₅ (6-) OC₂H₅

168 627 — S C₃H₇-n (6-) C₃H₇-n

145 628 — S C₃H₇-n (6-) OCH₃

158 629 — S C₃H₇-i (6-) OC₃H₇-i

155 630 — O C₃H₇-i (6-) OCH₃

145 631 — O C₃H₇-i (6-) OCH₃

111 632 — O C₃H₇-i (6-) OCH₃

122 633 — O C₃H₇-i (6-) OCH₃

171 634 — O C₃H₇-i (6-) OCH₃

160 635 — O C₃H₇-i (6-) OCH₃

142 636 — O C₂H₅ (6-) OC₂H₅

106 637 — O C₂H₅ (6-) OC₂H₅

106 638 — O C₂H₅ (6-) OC₂H₅

159 639 — O C₂H₅ (6-) OC₂H₅

148 640 — O C₂H₅ (6-) OC₂H₅

126 641 — O C₂H₅ (6-) OC₂H₅

111 642 — O C₂H₅ (6-) OC₂H₅

171 643 — O C₂H₅ (6-) OC₂H₅

127 644 — O C₂H₅ (6-) OC₂H₅

148 645 — O C₂H₅ (6-) OC₂H₅

123 646 — O C₃H₇-n (6-) OC₃H₇-n

138 647 — O C₃H₇-n (6-) OC₃H₇-n

 95 648 — O C₃H₇-n (6-) OC₃H₇-n

130 649 — O C₃H₇-n (6-) OC₃H₇-n

 74 650 — O C₃H₇-n (6-) OC₃H₇-n

109 651 — O C₃H₇-n (6-) OC₃H₇-n

 75 652 — O C₃H₇-n (6-) OC₃H₇-n

147 653 — O C₃H₇-n (6-) OC₃H₇-n

 99 654 — O C₃H₇-n (6-) OC₃H₇-n

102 655 — O C₃H₇-n (6-) OC₃H₇-n

 98 656 — O C₃H₇-i (6-) OC₃H₇-i

138 657 — O C₃H₇-i (6-) OC₃H₇-i

127 658 — O C₃H₇-i (6-) OC₃H₇-i

160 659 — O C₃H₇-i (6-) OC₃H₇-i

115 660 — O C₃H₇-i (6-) OC₃H₇-i

108 661 — O C₃H₇-i (6-) OC₃H₇-i

154 662 — O C₃H₇-i (6-) OC₃H₇-i

144 663 — O C₂H₄OC₂H₅ (6-) OCH₃

124 664 — O C₂H₄OC₂H₅ (6-) OCH₃

138 665 — O C₄H₉-n (6-) OCH₃

130 666 — O C₄H₉-n (6-) OCH₃

132 667 — O C₃H₇-i (6-) OC₃H₇-i

100 668 — O C₃H₇-i (6-) OC₃H₇-i

108 669 — O C₃H₇-i (6-) OC₃H₇-i

130 670 — O C₃H₇-i (6-) OC₃H₇-i

133 671 — O C₃H₇-i (6-) OC₃H₇-i

125 672 — O C₃H₇-i (6-) OC₃H₇-i

108 673 — O C₃H₇-i (6-) OC₃H₇-i

110 674 — O C₄H₉-n (6-) OCH₃

144 675 — O C₄H₉-n (6-) OCH₃

116 676 — O C₄H₉-n (6-) OCH₃

139 677 — O C₄H₉-n (6-) OCH₃

174 678 — O C₄H₉-n (6-) OCH₃

149 679 — O C₄H₉-n (6-) OCH₃

104 680 — O C₄H₉-n (6-) OCH₃

 98 681 — O C₄H₉-n (6-) OCH₃

112 682 — O C₄H₉-n (6-) OCH₃

100 683 — O C₄H₉-n (6-) OCH₃

 92 684 — O C₄H₉-n (6-) OCH₃

115 685 — O C₄H₉-n (6-) OCH₃

 99 686 — O C₄H₉-n (6-) OCH₃

102 687 — O C₄H₉-n (6-) OCH₃

106 688 — O C₂H₄OC₂H₅ (6-) OCH₃

120 689 — O C₂H₄OC₂H₅ (6-) OCH₃

 98 690 — O C₂H₄OC₂H₅ (6-) OCH₃

138 691 — O C₄H₉-i (6-) OC₂H₅

118 692 — O C₂H₄OC₂H₅ (6-) OCH₃

138 693 — O C₂H₄OC₂H₅ (6-) OCH₃

 94 694 — O C₂H₄OC₂H₅ (6-) OCH₃

 94 695 — O C₂H₄OC₂H₅ (6-) OCH₃

 65 696 — O C₂H₄OC₂H₅ (6-) OCH₃

 60 697 — O C₂H₄OC₂H₅ (6-) OCH₃

104 698 — O C₄H₉-n (6-) OC₄H₉-n

104 699 — O C₄H₉-n (6-) OC₄H₉-n

137 700 — O C₄H₉-n (6-) OC₄H₉-n

 70 701 — O C₄H₉-n (6-) OC₄H₉-n

110 702 — O C₄H₉-n (6-) OC₄H₉-n

102 703 — O C₃H₇-i (6-) OC₃H₇-i

137 704 — O C₃H₇-i (6-) OCH₃

160 705 — O C₃H₇-n (6-) OC₃H₇-n

 94 706 — O C₃H₇-n (6-) OC₂H₅

155 707 — O C₃H₇-n (6-) OC₂H₅

130 708 — O C₃H₇-n (6-) OC₂H₅

142 709 — O C₃H₇-n (6-) OC₂H₅

 85 710 — O C₃H₇-n (6-) OC₂H₅

106 711 — O C₃H₇-n (6-) OC₂H₅

 87 712 — S C₃H₇-i (6-) OCH₃

120 713 — S C₄H₉-n (6-) OCH₃

143 714 — S C₃H₇-i (6-) OC₃H₇-i

152 715 — S C₂H₄OC₂H₅ (6-) OCH₃

112 716 — S C₃H₇-i (6-) OCH₃

130 717 — S C₃H₇-i (6-) OCH₃

165 718 — S C₃H₇-i (6-) OC₃H₇-i

161 719 — S C₄H₉-n (6-) OCH₃

111 720 — S C₂H₅ (6-) OCH₃

156 721 — S C₂H₄OC₂H₅ (6-) OCH₃

137 722 — S CH₃ (6-) OCH₃

163 723 — S C₃H₇-n (6-) OCH₃

113 724 — S C₃H₇-n (6-) OCH₃

130 725 — S C₄H₉-n (6-) OCH₃

154 726 — S C₃H₇-i (6-) OC₃H₇-i

157 727 — S C₃H₇-n (6-) OC₃H₇-n

142 728 — S C₂H₅ (6-) OC₂H₅

162 729 — S CH₃ (6-) OCH₃

157 730 — S C₂H₅ (6-) OCH₃

108 731 — S CH₃ (6-) OCH₃

172 732 — S CH₃ (6-) OCH₃

147 733 — S C₃H₇-n (6-) OC₃H₇-n

160 734 — S C₃H₇-n (6-) OC₃H₇-n

103 735 — O C₃H₇-n (6-) OC₃H₇-n

172 736 — S C₂H₅ (6-) OC₂H₅

137 737 — S C₂H₅ (6-) OC₂H₅

156 738 — S C₂H₄OC₂H₅ (6-) OCH₃

103 739 — S C₃H₇-i (6-) OC₃H₇-i

134 740 — S C₄H₉-n (6-) OC₄H₉-n

 87 741 — S C₄H₉-n (6-) OC₄H₉-n

110 742 — S C₄H₉-n (6-) OC₄H₉-n

 88 743 — S C₄H₉-n (6-) OC₄H₉-n

 98 744 — S C₄H₉-n (6-) OC₄H₉-n

 98 745 — S C₄H₉-n (6-) OC₄H₉-n

 88 746 — S C₄H₉-n (6-) OC₄H₉-n

104 747 — S C₄H₉-n (6-) OC₄H₉-n

 75 748 — O C₂H₅ (6-) OC₂H₅

145 749 — S C₃H₇-i (6-) OC₂H₅

131 750 — S C₃H₇-i (6-) OC₂H₅

158 751 — S C₃H₇-i (6-) OC₂H₅

132 752 — S C₃H₇-i (6-) OC₂H₅

142 753 — S C₃H₇-i (6-) OC₂H₅

130 754 — S C₃H₇-i (6-) OC₂H₅

170 755 — S C₃H₇-n (6-) OC₂H₅

152 756 — S C₃H₇-n (6-) OC₂H₅

138 757 — S C₃H₇-n (6-) OC₂H₅

130 758 — S C₃H₇-n (6-) OC₂H₅

150 759 — S C₃H₇-n (6-) OC₂H₅

156 760 — S C₃H₇-n (6-) OC₂H₅

110 761 — S C₃H₇-n (6-) OC₂H₅

120 762 — S C₄H₉-n (6-) OC₄H₉-n

104 763 — S C₃H₇-i (6-) OCH₃

105 764 — S C₃H₇-n (6-) OC₃H₇-n

120 765 — S C₃H₇-n (6-) OCH₃

135 766 — S C₃H₇-n (6-) OC₃H₇-n

116 767 — S C₃H₇-i (6-) OC₃H₇-i

110 768 — S C₂H₄OC₂H₅ (6-) OCH₃

 95 769 — S C₃H₇-i (6-) OCH₃

112 770 — O C₃H₇-i (6-) OC₂H₅

 70 771 — O C₃H₇-i (6-) OC₂H₅

132 772 — O C₃H₇-i (6-) OC₂H₅

 75 773 — O C₃H₇-i (6-) OC₂H₅

118 774 — O C₃H₇-i (6-) OC₂H₅

 85 775 — O C₃H₇-i (6-) OC₂H₅

130 776 — O C₃H₇-i (6-) OC₂H₅

120 777 — O C₃H₇-i (6-) OC₂H₅

124 778 — O C₃H₇-i (6-) OC₂H₅

130 779 — O C₃H₇-i (6-) OC₂H₅

100 780 — O C₂H₅ (6-) OCH₃

172 781 — O C₂H₅ (6-) OCH₃

164 782 — O C₃H₇-i (6-) OC₃H₇-i

118 783 — O C₃H₇-i (6-) OC₃H₇-i

 88 784 — O C₄H₉-s (6-) OCH₃

124 785 — O C₄H₉-s (6-) OCH₃

100 786 — O C₄H₉-n (6-) OC₂H₅

106 787 — O C₄H₉-n (6-) OC₂H₅

108 788 — O C₄H₉-n (6-) OC₂H₅

105 789 — O C₄H₉-s (6-) OCH₃

112 790 — O C₄H₉-n (6-) OC₂H₅

 80 791 — O C₄H₉-s (6-) OCH₃

130 792 — O C₄H₉-n (6-) OC₂H₅

120 793 — O C₄H₉-n (6-) OC₂H₅

 95 794 — O C₄H₉-n (6-) OC₂H₅

 96 795 — O C₄H₉-s (6-) OCH₃

130 796 — O C₄H₉-s (6-) OCH₃

118 797 — O C₄H₉-s (6-) OCH₃

134 798 — O C₄H₉-s (6-) OCH₃

118 799 — O C₄H₉-n (6-) OC₂H₅

 90 800 — O C₄H₉-s (6-) OCH₃

 78 801 — O C₄H₉-s (6-) OCH₃

112 802 — O C₄H₉-s (6-) OCH₃

 78 803 — O C₄H₉-s (6-) OCH₃

 80 804 — O C₄H₉-n (6-) OC₄H₉-n

 55 805 — O C₄H₉-n (6-) OC₄H₉-n

100 806 — O C₄H₉-n (6-) OC₄H₉-n

 92 807 — O C₃H₇-n (6-) OC₂H₅

 74 808 — O C₃H₇-n (6-) OC₂H₅

143 809 — O C₃H₇-n (6-) OC₂H₅

102 810 — O C₃H₇-n (6-) OC₂H₅

 95 811 — O C₄H₉-n (6-) OC₄H₉-n

 82 812 — O C₄H₉-n (6-) OC₂H₅

 92 813 — O C₄H₉-n (6-) OCH₃

 90 814 — O C₄H₉-n (6-) OCH₃

124 815 — O C₄H₉-n (6-) OCH₃

 85 816 — O C₄H₉-n (6-) OCH₃

 90 817 — O C₂H₄OC₂H₅ (6-) OCH₃

 90 818 — O

(6-) OCH₃

165 819 — O

(6-) OCH₃

130 820 — O

(6-) OCH₃

149 821 — O C₄H₉-s (6-) OC₄H₉-s

125 822 — O

(6-) OCH₃

112 823 — O

(6-) OCH₃

156 824 — O

(6-) OCH₃

148 825 — O

(6-) OCH₃

145 826 — O

(6-) OCH₃

156 827 — O

(6-) OCH₃

126 828 — O

(6-) OCH₃

134 829 — O

(6-) OCH₃

114 830 — O

(6-) OCH₃

141 831 — O C₄H₉-i (6-) OC₂H₅

125 832 — O C₄H₉-i (6-) OC₂H₅

128 833 — O C₄H₉-i (6-) OC₂H₅

106 834 — O C₄H₉-i (6-) OC₂H₅

 88 835 — O C₄H₉-i (6-) OC₂H₅

112 836 — O C₄H₉-i (6-) OC₂H₅

125 837 — O C₄H₉-i (6-) OC₂H₅

106 838 — O H (6-) OH

172 839 — O C₄H₉-i (6-) OCH₃

102 840 — O C₄H₉-i (6-) OCH₃

114 841 — O C₄H₉-i (6-) OCH₃

124 842 — O C₄H₉-i (6-) OCH₃

 98 843 — O C₄H₉-i (6-) OCH₃

146 844 — O C₄H₉-i (6-) OCH₃

 97 845 — O C₄H₉-i (6-) OCH₃

117 846 — O C₄H₉-i (6-) OCH₃

142 847 — O C₄H₉-i (6-) OCH₃

109 848 — S C₂H₅ (6-) OCH₃

138 849 — S C₂H₅ (6-) OCH₃

135 850 — S C₂H₅ (6-) OCH₃

155 851 — S C₂H₅ (6-) OCH₃

160 852 — S C₄H₉-s (6-) OCH₃

108 853 — S C₄H₉-s (6-) OCH₃

143 854 — S C₄H₉-s (6-) OCH₃

105 855 — S C₄H₉-s (6-) OCH₃

 65 856 — S C₄H₉-s (6-) OCH₃

114 857 — O C₂H₅ (3-) CH₃

179 858 — S C₄H₉-s (6-) OCH₃

146 859 — S C₃H₇-i (6-) OCH₃

146 860 — S C₄H₉-n (6-) OCH₃

132 861 — S C₄H₉-n (6-) OCH₃

112 862 — S C₄H₉-n (6-) OCH₃

100 863 — S C₄H₉-n (6-) OCH₃

138 864 — S C₃H₇-i (6-) OC₂H₅

155 865 — S C₃H₇-i (6-) OC₂H₅

140 866 — S C₄H₉-n (6-) OCH₃

140 867 — O C₄H₉-i (6-) OCH₃

131 868 — O C₄H₉-i (6-) OCH₃

135 869 — O C₄H₉-i (6-) OCH₃

137 870 — O C₄H₉-n (6-) OC₄H₉-n

123 871 — O C₄H₉-n (6-) OC₂H₅

118 872 — O

(6-) OCH₃

164 873 — O C₃H₇-i (6-) OCH₃

150 874 — O C₃H₇-i (6-) OC₃H₇-i

148 875 — O C₃H₇-n (6-) OCH₃

147 876 — O C₂H₅ (6-) OC₂H₅

108 877 — O C₃H₇-i (6-) OC₃H₇-i

108 878 — O C₃H₇-i (6-) OC₃H₇-i

148 879 — O C₂H₅ (6-) OC₂H₅

176 880 — O C₃H₇-n (6-) OCH₃

144 881 — O C₃H₇-i (6-) OC₃H₇-i

167 882 — O C₂H₅ (6-) OC₂H₅

135 883 — O C₃H₇-n (6-) OCH₃

100 884 — O C₂H₅ (6-) OC₂H₅

158 885 — O C₃H₇-n (6-) OCH₃

108 886 — O C₃H₇-i (6-) OC₃H₇-i

164 887 — O C₃H₇-i (6-) OC₃H₇-i

157 888 — O C₃H₇-n (6-) OCH₃

113 889 — O C₃H₇-i (6-) OC₃H₇-i

132 890 — O C₃H₇-n (6-) OCH₃

 92 891 — O C₃H₇-i (6-) OC₃H₇-i

141 892 — O C₃H₇-i (6-) OC₃H₇-i

159 893 — O C₂H₅ (6-) OC₂H₅

139 894 — O C₂H₅ (6-) OC₂H₅

150 895 — O C₃H₇-n (6-) OCH₃

126 896 — O C₃H₇-i (6-) CH₃

148 897 — O C₃H₇-i (6-) CH₃

157 898 — O C₃H₇-i (6-) CH₃

125 899 NH O CH₃ (6-) OCH₃

182 900 NH O CH₃ (6-) OCH₃

175 901 — O CF₃ (6-) CH₃

198 (Na salt) 902 — O CF₃ (6-) CH₃

129 903 — O CF₃ (6-) CH₃

149 904 — O CF₃ (6-) CH₃

163 905 — O CF₃ (6-) C₂H₅

121 906 — O C₃H₇-i (6-) CH₃

170 907 — O C₃H₇-i (6-) CH₃

125 908 — O C₃H₇-i (6-) CH₃

129 909 — O C₃H₇-i (6-) CH₃

156 910 — O CH₃ (6-) OCH₃

157 911 — O CH₃ (6-) OCH₃

177 912 — O CH₃ (6-) OCH₃

172 913 — O C₃H₇-i (6-) CH₃

132 914 — O C₃H₇-i (6-) CH₃

153 915 — O C₃H₇-i (6-) CH₃

150 916 — O C₃H₇-i (6-) CH₃

110 917 — O C₃H₇-i (6-) CH₃

131 918 — O C₃H₇-i (6-) CH₃

133 919 — O CH₃ (6-) OCH₃

153 920 — O C₃H₇-i (6-) CH₃

122 921 — O C₃H₇-i (6-) CH₃

147 922 — O CH₃ (6-) OCH₃

160 923 — O CH₃ (6-) OCH₃

182 924 — O CH₃ (6-) OCH₃

142 925 — O CH₃ (6-) OCH₃

178 926 — O C₃H₇-i (6-) CH₃

151 927 — O CH₃ (6-) OCH₃

178 928 — O CH₃ (6-) OCH₃

130 929 — O CH₃ (6-) OCH₃

124 930 — O CH₃ (6-) OCH₃

153 931 — O CH₃ (6-) OCH₃

157 932 — O CH₃ (6-) OCH₃

114 933 — O CH₃ (6-) OCH₃

130 934 — O C₃H₇-i (6-) CH₃

151 935 — O C₃H₇-i (6-) CH₃

153 936 — O CH₃ (6-) OCH₃

167 937 — O CF₂Cl (6-) CH₃

180 (Na salt) 938 — O CH₃ (6-) OCH₃

157 (Na salt) 939 NH O CH₂CH₂F (6-) CH₃

163 940 NH O CH₂CHF₂ (6-) CH₃

160 941 NH O CF₂CHFCl (6-) CH₃

 88 942 — O CH₂CH₂F (6-) CH₃

178 943 — O CH₂CH₂F (6-) CH₃

135 944 — O CH₂CH₂F (6-) CH₃

127 945 — O CH₂CH₂F (6-) CH₃

139 946 — O CH₂CH₂F (6-) CH₃

280 (Na salt) 947 — O CH₂CH₂F (6-) CH₃

171 948 — O CH₂CH₂F (6-) CH₃

144 949 — O CH₂CHF₂ (6-) CH₃

273 (Na salt) 950 — O CH₂CHF₂ (6-) CH₃

181 951 — O CH₂CHF₂ (6-) CH₃

142 952 — O CH₂CHF₂ (6-) CH₃

114 953 — O CH₂CHF₂ (6-) CH₃

108 954 — O CH₂CHF₂ (6-) CH₃

185 955 — O CH₂CHF₂ (6-) CH₃

150 956 — O CF₃ (6-) C₂H₅

143 (Na salt) 957 — O CF₃ (6-) CH₃

155 958 — O CF₃ (6-) CH₃

112 959 — O CF₃ (6-) CH₃

166 960 — O CF₃ (6-) CH₃

137 961 — O CF₃ (6-) CH₃

132 962 — O CF₃ (6-) CH₃

172 963 — O CF₃ (6-) CH₃

139 964 — O CF₃ (6-) CH₃

130 965 — O C₂H₅ (3-) CH₃

184

TABLE 1A Examples of the compounds of the formula (IA) (IA)

Ex. (Position-) Melting No. A Q R¹ R² Q¹ R⁴ R⁵ point ° C. 966 NH O C₄H₉ (6-)CH₃ O

OC₂H₅ 121 967 NH O CH₂CH(CH₃)₂ (6-)CH₃ O

OC₂H₅ 127 968 NH O CH₂CF₃ (6-)CH₃ O CH₃ OCH₃ 164 969 NH O CH₂CF₃ (6-)CH₃ O CH₃ OC₂H₅ 138 970 NH O CH₂CF₃ (6-)CH₃ O CH₃ OC₃H₇ 123 971 NH O CH₂CF₃ (6-)CH₃ O CH₃ OCH(CH₃)₂ 141 972 — O CH₂CH₂F (3-)Cl O CH₃ OC₂H₅ 139 973 — O CH₂CH₂F (3-)CH₃ O CH₃ OC₂H₅ 154 974 — O C₃H₇-i (6-)CF₃ O

C₄H₉-s 975 — O C₃H₇-i (6-)CF₃ O CH₃ C₄H₉-s 976 — O C₃H₇-i (6-)CF₃ O CH₃ C₄H₉ 977 — O C₃H₇-i (6-)CF₃ O CH₃ C₄H₉-i 978 — S C₃H₇-i (6-)CF₃ O CH₃ C₂H₅ 979 — S C₃H₇ (6-)CH₃ O

OC₂H₅ 980 — S C₃H₇ (6-)CH₃ O C₂H₅ OC₂H₅ 981 — S C₃H₇-i (6-)CH₃ O

OC₂H₅ 982 — S C₃H₇-i (6-)CH₃ O C₂H₅ OC₂H₅ 983 — S C₃H₇ (6-)CH₃ O CH₃ OC₃H₇-i 984 — S C₃H₇-i (6-)CH₃ O CH₃ OC₃H₇-i 985 — S C₃H₇ (6-)CH₃ O CH₃ OC₃H₇ 986 — S C₃H₇-i (6-)CH₃ O CH₃ OC₃H₇ 987 — S C₃H₇ (6-)CH₃ O

OCH₃ 988 — O CH₃ (6-)CF₃ O

C₄H₉-s 989 — O C₂H₅ (6-)CF₃ O

C₄H₉-s 990 — O C₃H₇ (6-)CF₃ O

C₄H₉-s 991 — O CH₃ (6-)CF₃ O CH₃ C₄H₉-s 992 — O C₂H₅ (6-)CF₃ O CH₃ C₄H₉-s 993 — O CH₃ (6-)CF₃ O CH₃ C₄H₉ 994 — O CH₃ (6-)CF₃ O

C₄H₉-t 995 — O CH₃ (6-)CF₃ O

OC₃H₇ 996 — O C₂H₅ (6-)CF₃ O

OC₃H₇ 997 — O C₃H₇ (6-)CF₃ O

OC₃H₇ 998 — O C₂H₅ (6-)CF₃ O CH₃ C₄H₉ 999 — O C₃H₇ (6-)CF₃ O CH₃ C₄H₉ 1000 — O CH₃ (6-)CF₃ O CH₃ C₄H₉-i 1001 — S CH₃ (6-)CF₃ O CH₃ SCH₃ 1002 — S CH₃ (6-)CF₃ O

OC₂H₅ 1003 — S CH₃ (6-)CF₃ O CH₃ OC₃H₇-i 1004 — S CH₃ (6-)CF₃ O C₂H₅ OC₂H₅ 1005 — S CH₃ (6-)CF₃ O

OC₃H₇ 1006 — S CH₃ (6-)CF₃ O

OC₃H₇-i 1007 — S CH₃ (6-)CF₃ O CH₃ OCH₂CF₃ 1008 — S CH₃ (6-)CF₃ O CH₃ OC₃H₇ 1009 — S CH₃ (6-)CF₃ O

1010 — S CH₃ (6-)CF₃ O

OCH₃ 1011 — S CH₃ (6-)CF₃ O

OCH₂CF₃ 1012 — S CH₃ (6-)CH₃ O CH₃ CH₃ 1013 — S CH₃ (6-)CH₃ O CH₃ OCH₃ 1014 — S CH₃ (6-)CH₃ O CH₃ OC₂H₅ 1015 — S CH₃ (6-)CH₃ O CH₃ OH₅ 1016 — S C₂H₅ (6-)CH₃ O CH₃ C₂H₅ 1017 — S CH₃ (6-)CH₃ O CH₃ SCH₃ 1018 — S C₂H₅ (6-)CH₃ O CH₃ SCH₃ 1019 — S CH₃ (6-)CH₃ O

OC₂H₅ 1020 — S C₂H₅ (6-)CH₃ O

OC₂H₅ 1021 — S CH₃ (6-)CH₃ O CH₃ OC₃H₇-i 1022 — S C₂H₅ (6-)CH₃ O

OC₃H₇ 1023 — O CH₃ (6-)CF₃ O

OCH₂CF₃ 1024 — O CH₃ (6-)CF₃ O

C₃H₇-i 1025 — O CH₃ (6-)CF₃ O CH₃ C₄H₉-t 1026 — O CH₃ (6-)CF₃ O

C₃H₇ 1027 — O CH₃ (6-)CF₃ O

C₃H₇-i 1028 — O CH₃ (6-)CF₃ O C₂H₅ C₂H₅ 1029 — O CH₃ (6-)CF₃ O C₃H₇ C₂H₅ 1030 — O CH₃ (6-)CF₃ O C₃H₇-i C₂H₅ 1031 — O CH₃ (6-)CF₃ O C₂H₅ C₃H₇ 1032 — O CH₃ (6-)CF₃ O C₃H₇ C₃H₇ 1033 — O CH₃ (6-)CF₃ O N(CH₃)₂ CH₃ 1034 — O CH₃ (6-)CF₃ O CH₃ H 1035 — O CH₃ (6-)CF₃ O CH₃ CH₂CH₂O 1036 — O CH₃ (6-)CF₃ O CH₃

1037 — O CH₃ (6-)CF₃ O C₃H₇-i C₃H₇ 1038 — O CH₃ (6-)CF₃ O C₂H₅ C₃H₇-i 1039 — O CH₃ (6-)CF₃ O C₃H₇ C₃H₇-i 1040 — O CH₃ (6-)CF₃ O C₃H₇-i C₃H₇-i 1041 — O CH₃ (6-)CF₃ O C₂H₅

1042 — O CH₃ (6-)CF₃ O C₃H₇

1043 — O CH₃ (6-)CF₃ O C₃H₇-i

1044 — O C₂H₅ (6-)CF₃ O C₃H₇-i

1045 — O C₃H₇ (6-)CF₃ O C₃H₇-i

1046 — O CH₃ (6-)CF₃ O CH₃ OCH₂CF₂CHF₂ 1047 — O C₃H₇ (6-)CF₃ O CH₃ OCH₂CF₂CHF₂ 1048 — O CH₃ (6-)CF₃ O CH₃ OC₆H₁₁ 1049 — O C₂H₅ (6-)CF₃ O CH₃ OC₆H₁₁ 1050 — O C₃H₇ (6-)CF₃ O CH₃ OC₆H₁₁ 1051 — O CH₃ (6-)CF₃ O CH₃

1052 — O CH₃ (6-)CF₃ O

C₄H₉-i 1053 — O CH₃ (6-)CF₃ O

C₄H₉ 1054 — O CH₃ (6-)CF₃ O

CH₃ 1055 — O CH₃ (6-)CF₃ O

C₂H₅ 1056 — O CH₃ (6-)CF₃ O

1057 — O CH₃ (6-)CF₃ O C₂H₅ CH₃ 1058 — O C₃H₇-i (6-)CF₃ O C₃H₇-i

1059 — O C₃H₇-i (6-)CF₃ O CH₃ OCH₂CF₂CHF₂ 1060 — O C₃H₇ (6-)CF₃ O CH₃ CH₃ 1061 — O C₃H₇ (6-)CF₃ O CH₃ C₃H₇-i 1062 — O C₃H₇ (6-)CF₃ O CH₃ CH₂OCH₃ 1063 — O C₃H₇ (6-)CF₃ O CH₃ Br 1064 — O C₂H₅ (6-)CF₃ O CH₃ OCH₂CF₃ 1065 — O C₃H₇ (6-)CF₃ O OCH₃ C₃H₇ 1066 — O C₃H₇ (6-)CF₃ O

Br 1067 — O C₂H₅ (6-)CF₃ O

CH₂OCH₃ 1068 — O C₃H₇ (6-)CF₃ O

CH₂OCH₃ 1069 — S C₂H₅ (6-)CF₃ O CH₃ SCH₃ 1070 — S C₃H₇ (6-)CF₃ O CH₃ SCH₃ 1071 — S C₃H₇-i (6-)CF₃ O CH₃ SCH₃ 1072 — S C₂H₅ (6-)CF₃ O

OC₂H₅ 1073 — S C₃H₇ (6-)CF₃ O

OC₂H₅ 1074 — S C₃H₇-i (6-)CF₃ O

OC₂H₅ 1075 — S C₂H₅ (6-)CF₃ O CH₃ OC₃H₇-i 1076 — S C₃H₇ (6-)CF₃ O CH₃ OC₃H₇-i 1077 — S C₃H₇-i (6-)CF₃ O CH₃ OC₃H₇-i 1078 — S C₂H₅ (6-)CF₃ O C₂H₅ OC₂H₅ 1079 — S C₃H₇ (6-)CF₃ O C₂H₅ OC₂H₅ 1080 — S C₃H₇-i (6-)CF₃ O C₂H₅ OC₂H₅ 1081 — S C₂H₅ (6-)CF₃ O

OC₃H₇ 1082 — S C₃H₇ (6-)CF₃ O

OC₃H₇ 1083 — S C₃H₇-i (6-)CF₃ O

OC₃H₇ 1084 — O C₃H₇-i (6-)CF₃ O

C₄H₉-t 1085 — O C₂H₅ (6-)CF₃ O CH₃ OC₄H₉-s 1086 — O C₃H₇ (6-)CF₃ O CH₃

1087 — O C₃H₇-i (6-)CF₃ O CH₃ OC₄H₉-s 1088 — O C₂H₅ (6-)CF₃ O CH₃ OC₆H₅ 1089 — O C₃H₇ (6-)CF₃ O CH₃ OC₆H₅ 1090 — O C₃H₇-i (6-)CF₃ O CH₃ OC₆H₅ 1091 — O C₂H₅ (6-)CF₃ O CH₂CH═CH₂ OCH₂CF₃ 1092 — O C₃H₇ (6-)CF₃ O CH₂CH═CH₂ OCH₂CF₃ 1093 — O C₃H₇-i (6-)CF₃ O CH₂CH═CH₂ OCH₂CF₃ 1094 — O C₂H₅ (6-)CF₃ O CH₃ OCH₂C₂H₅ 1095 — O C₃H₇ (6-)CF₃ O CH₃ OCH₂C₆H₅ 1096 — O C₃H₇-i (6-)CF₃ O CH₃ OCH₂C₆H₅ 1097 — O C₂H₅ (6-)CF₃ O N(CH₃)₂ CH₃ 1098 — O C₃H₇ (6-)CF₃ O N(CH₃)₂ CH₃ 1099 — O C₃H₇-i (6-)CF₃ O N(CH₃)₂ CH₃ 1100 — O C₃H₇ (6-)CF₃ O CH₃ H 1101 — O C₂H₅ (6-)CF₃ O CH₃ CH₂CH₂OC₃H₇-i 1102 — O C₃H₇-i (6-)CF₃ O CH₃ CH₂CH₂OC₃H₇-i 1103 — O OH (6-)CF₃ O CH₃

1104 — O C₃H₇ (6-)CF₃ O CH₃

1105 — O C₃H₇-i (6-)CF₃ O CH₃

1106 — O C₂H₅ (6-)CF₃ O CH₃ OCH₂CF₂CHF₂ 1107 — S C₃H₇-i (6-)CH₃ O

OCH₃ 1108 — S C₃H₇ (6-)CH₃ O

OC₃H₇-i 1109 — S C₃H₇-i (6-)CH₃ O

OC₃H₇-i 1110 — S C₃H₇ (6-)CH₃ O

OC₃H₇ 1111 — S C₃H₇-i (6-)CH₃ O

OC₃H₇ 1112 — O C₂H₅ (6-)CF₃ O

C₄H₉-i 1113 — O C₃H₇ (6-)CF₃ O

C₄H₉-i 1114 — O C₃H₇-i (6-)CF₃ O

C₄H₉-i 1115 — O C₂H₅ (6-)CF₃ O

C₄H₉ 1116 — O C₃H₇ (6-)CF₃ O

C₄H₉ 1117 — O C₃H₇-i (6-)CF₃ O

C₄H₉ 1118 — O C₂H₅ (6-)CF₃ O

CH₃ 1119 — O C₃H₇ (6-)CF₃ O

CH₃ 1120 — O C₃H₇-i (6-)CF₃ O

CH₃ 1121 — O C₂H₅ (6-)CF₃ O

C₂H₅ 1122 — O C₃H₇ (6-)CF₃ O

C₂H₅ 1123 — O C₃H₇-i (6-)CF₃ O

C₂H₅ 1124 — O C₂H₅ (6-)CF₃ O

1125 — O C₃H₇ (6-)CF₃ O

1126 — O C₃H₇-i (6-)CF₃ O

1127 — O C₂H₅ (6-)CF₃ O C₃H₇

1128 — O C₃H₇ (6-)CF₃ O C₃H₇

1129 — O C₃H₇-i (6-)CF₃ O C₃H₇

1130 — O C₂H₅ (6-)CF₃ O C₂H₅ CH₃ 1131 — O C₃H₇ (6-)CF₃ O C₂H₅ CH₃ 1132 — O C₃H₇-i (6-)CF₃ O C₂H₅ CH₃ 1133 — O C₂H₅ (6-)CF₃ O

C₃H₇ 1134 — O C₃H₇ (6-)CF₃ O

C₃H₇ 1135 — O C₃H₇-i (6-)CF₃ O

C₃H₇ 1136 — O C₂H₅ (6-)CF₃ O

C₃H₇-i 1137 — O C₃H₇ (6-)CF₃ O

C₃H₇-i 1138 — O C₃H₇-i (6-)CF₃ O

C₃H₇-i 1139 — O C₂H₅ (6-)CF₃ O C₂H₅ C₂H₅ 1140 — O C₃H₇ (6-)CF₃ O C₂H₅ C₂H₅ 1141 — O C₃H₇-i (6-)CF₃ O C₂H₅ C₂H₅ 1142 — O C₂H₅ (6-)CF₃ O C₃H₇ C₂H₅ 1143 — O C₃H₇ (6-)CF₃ O C₃H₇ C₂H₅ 1144 — O C₃H₇-i (6-)CF₃ O C₃H₇ C₂H₅ 1145 — S C₂H₅ (6-)CF₃ O

OC₃H₇-i 1146 — S C₃H₇ (6-)CF₃ O

OC₃H₇-i 1147 — S C₃H₇-i (6-)CF₃ O

OC₃H₇-i 1148 — S C₂H₅ (6-)CF₃ O CH₃ OCH₂CF₃ 1149 — S C₃H₇ (6-)CF₃ O CH₃ OCH₂CF₃ 1150 — S C₃H₇-i (6-)CF₃ O CH₃ OCH₂CF₃ 1151 — S C₂H₅ (6-)CF₃ O CH₃ OC₃H₇ 1152 — S C₃H₇ (6-)CF₃ O CH₃ OC₃H₇ 1153 — S C₃H₇-i (6-)CF₃ O CH₃ OC₃H₇ 1154 — S C₂H₅ (6-)CF₃ O

1155 — S C₃H₇ (6-)CF₃ O

1156 — S C₃H₇-i (6-)CF₃ O

1157 — S C₂H₅ (6-)CF₃ O

OCH₃ 1158 — S C₃H₇ (6-)CF₃ O

OCH₃ 1159 — S C₃H₇-i (6-)CF₃ O

OCH₃ 1160 — S C₂H₅ (6-)CF₃ O

OCH₂CF₃ 1161 — S C₃H₇ (6-)CF₃ O

OCH₂CF₃ 1162 — S C₃H₇-i (6-)CF₃ O

OCH₂CF₃ 1163 — O C₂H₅ (6-)CF₃ O C₃H₇-i C₃H₇ 1164 — O C₃H₇ (6-)CF₃ O C₃H₇-i C₃H₇ 1165 — O C₃H₇-i (6-)CF₃ O C₃H₇-i C₃H₇ 1166 — O C₂H₅ (6-)CF₃ O C₂H₅ C₃H₇-i 1167 — O C₃H₇ (6-)CF₃ O C₂H₅ C₃H₇-i 1168 — O C₃H₇-i (6-)CF₃ O C₂H₅ C₃H₇-i 1169 — O C₂H₅ (6-)CF₃ O C₃H₇ C₃H₇-i 1170 — O C₃H₇ (6-)CF₃ O C₃H₇ C₃H₇-i 1171 — O C₃H₇-i (6-)CF₃ O C₃H₇ C₃H₇-i 1172 — O C₂H₅ (6-)CF₃ O C₃H₇-i C₃H₇-i 1173 — O C₃H₇ (6-)CF₃ O C₃H₇-i C₃H₇-i 1174 — O C₃H₇-i (6-)CF₃ O C₃H₇-i C₃H₇-i 1175 — O C₂H₅ (6-)CF₃ O C₃H₇-i C₂H₅ 1176 — O C₃H₇ (6-)CF₃ O C₃H₇-i C₂H₅ 1177 — O C₃H₇-i (6-)CF₃ O C₃H₇-i C₂H₅ 1178 — O C₂H₅ (6-)CF₃ O C₂H₅ C₃H₇ 1179 — O C₃H₇ (6-)CF₃ O C₂H₅ C₃H₇ 1180 — O C₃H₇-i (6-)CF₃ O C₂H₅ C₃H₇ 1181 — O C₂H₅ (6-)CF₃ O C₃H₇ C₃H₇ 1182 — O C₃H₇ (6-)CF₃ O C₃H₇ C₃H₇ 1183 — O C₃H₇-i (6-)CF₃ O C₃H₇ C₃H₇ 1184 — O C₂H₅ (6-)CF₃ O CH₃ C₄H₉-t 1185 — O C₃H₇ (6-)CF₃ O CH₃ C₄H₉-t 1186 — O C₃H₇-i (6-)CF₃ O CH₃ C₄H₉-t 1187 — O C₂H₅ (6-)CF₃ O

C₄H₉-t 1188 — O C₃H₇ (6-)CF₃ O

C₄H₉-t 1189 — O C₂H₅ (6-)CF₃ O C₂H₅

1190 — O C₃H₇ (6-)CF₃ O C₂H₅

1191 — O C₃H₇-i (6-)CF₃ O C₂H₅

1192 — O C₃H₇-i (6-)CF₃ O CH₃ OC₆H₁₁ 1193 — S C₃H₇ (6-)CH₃ O CH₃ OCH₂CF₃ 1194 — S C₃H₇-i (6-)CH₃ O CH₃ OCH₂CF₃ 1195 — S C₃H₇ (6-)CH₃ O

OCH₂CF₃ 1196 — S C₃H₇-i (6-)CH₃ O

OCH₂CF₃ 1197 — S C₃H₇-i (6-)CH₃ O CH₃ C₂H₅ 1198 — S CH₃ (6-)CF₃ O CH₃ C₂H₅ 1199 — S C₂H₅ (6-)CF₃ O CH₃ C₂H₅ 1200 — S C₃H₇ (6-)CF₃ O CH₃ C₂H₅ 1201 — O C₂H₅ (6-)CF₃ O

H 1202 — O CH₃ (6-)CF₃ O

H 1203 — O C₃H₇ (6-)CF₃ O

H 1204 — O C₃H₇-i (6-)CF₃ O

H 1205 — O C₂H₅ (6-)CF₃ O

OCH₃ 1206 — O C₃H₇ (6-)CF₃ O

OCH₃ 1207 — O C₃H₇-i (6-)CF₃ O

OCH₃ 1208 — O CH₃ (6-)CF₃ O CH₂CH═CH₂ OC₃H₇ 1209 — O C₂H₅ (6-)CF₃ O CH₂CH═CH₂ OC₃H₇ 1210 — O CH₃ (6-)CF₃ O CH₃ OCH₂C₄H₉-t 1211 — O C₂H₅ (6-)CF₃ O CH₃ OCH₂C₄H₉-t 1212 — O C₃H₇ (6-)CF₃ O CH₃ OCH₂C₄H₉-t 1213 — O C₃H₇-i (6-)CF₃ O CH₃ OCH₂C₄H₉-t 1214 — O CH₃ (6-)CF₃ O CH₃ OCH₂CCl₃ 1215 — O C₂H₅ (6-)CF₃ O CH₃ OCH₂CCl₃ 1216 — O C₃H₇ (6-)CF₃ O CH₃ OCH₂CCl₃ 1217 — O C₃H₇-i (6-)CF₃ O CH₃ OCH₂CCl₃ 1218 — O CH₃ (6-)CF₃ O

CH═CHCH₃ 1219 — O C₂H₅ (6-)CF₃ O

CH═CHCH₃ 1220 — O CH₃ (4-)CH₃ O CH₃ SCH₃ 1221 — O CH₃ (4-)CH₃ O CH₃ OC₂H₅ 1222 — O CH₃ (4-)CH₃ O

OC₂H₅ 1223 — O CH₃ (4-)CH₃ O

OC₃H₇ 1224 — O CH₃ (4-)CH₃ O CH₃ OC₃H₇ 1225 — O CH₃ (4-)CH₃ O

OCH₃ 1226 — O CH₃ (6-)CF₃ O CH₃ OCH₂C₆H₅ 1227 — O CH₃ (6-)CF₃ O

CH═CHCH₃ 1228 — O CH₃ (6-)CF₃ O CH₃ CH₂CH₂OCH₃ 1229 — O C₂H₅ (6-)CF₃ O CH₃ CH₂CH₂OCH₃ 1230 — O C₂H₅ (6-)CF₃ O

CH═CHCH₃ 1231 — O C₃H₇ (6-)CF₃ O

CH═CHCH₃ 1232 — O C₃H₇-i (6-)CF₃ O CH₃ CH₂CH₂OCH₃ 1233 — O C₃H₇-i (6-)CF₃ O

CH═CHCH₃ 1234 — S CH₃ (6-)CH₃ O

OC₃H₇-i 1235 — S CH₃ (6-)CH₃ O CH₃ OCH₂CF₃ 1236 — S CH₃ (6-)CH₃ O CH₃ OC₃H₇ 1237 — S CH₃ (6-)CH₃ O

OCH₃ 1238 — S C₂H₅ (6-)CH₃ O

OC₃H₇-i 1239 — S C₂H₅ (6-)CH₃ O CH₃ OCH₂CF₃ 1240 — S C₂H₅ (6-)CH₃ O CH₃ OC₃H₇ 1241 — S C₂H₅ (6-)CH₃ O

OCH₃ 1242 — S C₂H₅ (6-)CH₃ O

OCH₂CF₃ 1243 — S CH₃ (6-)CH₃ O

1244 — S C₂H₅ (6-)CH₃ O

1245 — S C₃H₇ (6-)CH₃ O

1246 — S C₃H₇-i (6-)CH₃ O

1247 — O CH₃ (6-)CF₃ O

OCH₃ 1248 — O CH₂CH₂F (6-)CF₃ O CH₃ OCH₃ 1249 — O CH₂CH₂F (6-)CF₃ O CH₃ OC₂H₅ 1250 — O CH₂CH₂F (6-)CF₃ O

OC₂H₅ 1251 — O CH₂CH₂F (6-)CF₃ O CH₃ OC₃H₇ 1252 — O CH₂CH₂F (6-)CF₃ O CH₃ OC₃H₇-i 1253 — O CH₂CH₂F (6-)CF₃ O

OC₃H₇ 1254 — O CH₂CH₂F (6-)CF₃ O

OC₃H₇-i 1255 — O CH₂CH₂F (6-)CF₃ O

1256 — O CH₃ (6-)C₂H₅ O CH₃ CH₂OCH₃ 124 1257 — O CH₃ (6-)C₂H₅ O CH₃ OCH₂CF₃ 156 1258 — O CH₃ (6-)C₂H₅ O CH₃ SC≡CH 147 1259 — O CH₃ (6-)C₂H₅ O CH₃ CH(CH₃)₂ 113 1260 — O CH₃ (6-)C₂H₅ O CH₃ CH(CH₃)₂ 125 1261 — O CH₃ (6-)C₂H₅ O

Br 154 1262 — O CH₃ (6-)C₂H₅ O C₂H₅ OC₂H₅ >250 1263 — O CH₃ (6-)C₂H₅ O CH₃ OC₃H₇ 200 1264 — O CH₃ (6-)C₂H₅ O

OC₂H₅ 178 1265 — O CH₃ (6-)Br O CH₃ OC₂H₅ 228 1266 — O C₂H₅ (6-)C₂H₅ O C₂H₅ OC₂H₅ 1267 — O C₂H₅ (6-)C₂H₅ O CH₃ OC₃H₇ 1268 — O CH(CH₃)₂ (6-)C₂H₅ O C₂H₅ OC₂H₅ 1269 — O CH(CH₃)₂ (6-)C₂H₅ O CH₃ OC₃H₇ 1270 — O C₂H₅ (6-)C₂H₅ O CH₃ CH₂OCH₃ 1271 — O C₂H₅ (6-)C₂H₅ O CH₃ OCH₂CF₃ 1272 — O CH(CH₃)₂ (6-)C₂H₅ O CH₃ CH₂OCH₃ 1273 — O CH(CH₃)₂ (6-)C₂H₅ O CH₃ OCH₂CF₃ 1274 — O CF₃ (6-)Br O CH₃ OC₂H₅ 1275 — O C₂H₅ (6-)C₂H₅ O CH₃ OCH(CH₃)₂ 1276 — O C₂H₅ (6-)C₂H₅ O

OC₂H₅ 1277 — O C₂H₅ (6-)C₂H₅ O

CH₂OCH₃ 1278 — O CH(CH₃)₂ (6-)C₂H₅ O CH₃ OCH(CH₃)₂ 1279 — O CH(CH₃)₂ (6-)C₂H₅ O

OC₂H₅ 1280 — O CH(CH₃)₂ (6-)C₂H₅ O

CH₂OCH₃ 1281 — O C₃H₇ (6-)Br O CH₃ OC₂H₅ 1282 — O C₂H₅ (6-)C₂H₅ O CH₃ OCH₃ 1283 — O C₂H₅ (6-)F O CH₃ OC₂H₅ 165 1284 — O CH₃ (6-)F O CH₃ OC₂H₅ 211 1285 — O CH₃ (6-)CN O CH₃ OC₂H₅ 255 1286 — O CH₃ (6-)CN O CH₃ OC₂H₅ 1287 — O CH₃ (6-)CN O CH₃ C₂H₅ 162 1288 — O CH₃ (6-)CN O CH₃ SCH₃ 268 1289 — O CH₃ (6-)CN O CH₃ OCH₃ 242 1290 — O CH₃ (6-)CH(CH₃)₂ O CH₃ OCH₃ 183 1291 — O C₂H₅ (6-)CH(CH₃)₂ O CH₃ CH₃ 283 1292 — O C₂H₅ (6-)CH(CH₃)₂ O CH₃ OCH₃ 227 1293 — O CH₃ (6-)F O CH₃ OC₂H₅ 1294 — O CH₃ (6-)F O CH₃ C₂H₅ 156 1295 — O CH₃ (6-)F O CH₃ SCH₃ 179 1296 — O CH₃ (6-)F O CH₃ CH₃ 217 1297 — O CH₃ (6-)F O

OCH(CH₃)₂ 147 1298 — O CH(CH₃)₂ (6-)F O CH₃ OC₂H₅ 165 1299 — O CH(CH₃)₂ (6-)F O CH₃ C₂H₅ 113 1300 — O CH(CH₃)₂ (6-)F O CH₃ OCH₃ 149 1301 — O CH(CH₃)₂ (6-)F O

CH₃ 147 1302 — O CH(CH₃)₂ (6-)F O

OCH(CH₃)₂ 127 1303 — O C₃H₇ (6-)F O CH₃ OC₂H₅ 139 1304 — O C₃H₇ (6-)F O CH₃ C₂H₅ 116 1305 — O C₃H₇ (6-)F O CH₃ OCH₃ 129 1306 — O C₃H₇ (6-)F O

CH₃ 120 1307 — O C₃H₇ (6-)F O CH₃ OC₂H₅ >160 1308 — O C₂H₅ (6-)CH₃ O CH₃ OC₄H₉ 114 1309 — O C₂H₅ (6-)CH₃ O

OC₄H₉ 126 1310 — O C₂H₅ (6-)CH₃ O CH₃ OCH₂CH(CH₃)₂ 144 1311 — O C₂H₅ (6-)CH₃ O

OCH₂CH(CH₃)₂ 145 1312 — O C₂H₅ (6-)CH₃ O

OCH₂CF₃ 133 1313 — O C₂H₅ (6-)CH₃ O

OCH₃ 181 1314 — O C₂H₅ (6-)CH(CH₃)₂ O CH₃ OC₄H₉ 170 1315 — O C₂H₅ (6-)CH(CH₃)₂ O

OC₄H₉ 129 1316 — O CH₃ (6-)CH₃ O CH₃ OCH₂CH(CH₃)₂ 137 1317 — O CH₃ (6-)CH₃ O

OCH₂CH(CH₃)₂ 165 1318 — O CH₃ (6-)CH₃ O CH₃

150 1319 — O CH₃ (6-)CH₃ O

186 1320 — O C₂H₅ (6-)CH(CH₃)₂ O CH₃ OCH₂CH(CH₃)₂ 163 1321 — O C₂H₅ (6-)CH(CH₃)₂ O CH₃

134 1322 — O C₂H₅ (6-)CH(CH₃)₂ O

187 1323 — O C₂H₅ (6-)CH(CH₃)₂ O

CH₃ 158 1324 — O C₂H₅ (6-)CH(CH₃)₂ O

C₂H₅ 172 1325 — O C₂H₅ (6-)CH(CH₃)₂ O

C₃H₇ 142 1326 — O C₂H₅ (6-)CH(CH₃)₂ O

OCH₂CF₃ 150 1327 — O C₂H₅ (6-)CH(CH₃)₂ O

OCH₃ 137 1328 — O C₂H₅ (6-)CH(CH₃)₂ O

CH(C₂H₃)₂ 168 1329 — O C₂H₅ (6-)CH₃ O

SCH₃ 167 1330 — O CH(CH₃)₂ (6-)CH₃ O

SCH₃ 167 1331 — O C₂H₅ (6-)CH₃ O

SC₂H₅ 150 1332 — O CH(CH₃)₂ (6-)CH₃ O

SC₂H₅ 150 1333 — O C₃H₇ (6-)CH₃ O

SC₂H₅ 140 1334 — O C₂H₅ (6-)F O CH₃ SCH₃ 165 1335 — O C₂H₅ (6-)F O CH₃ C₂H₅ 135 1336 — O C₂H₅ (6-)F O CH₃ OCH₃ 168 1337 — O C₂H₅ (6-)F O CH₃ CH₃ 140 1338 — O C₂H₅ (6-)F O

OCH₃ 138 1339 — O C₃H₇ (6-)OC₃H₇ O CH₃ OC₂H₅ 1340 — O C₃H₇ (6-)OC₃H₇ O CH₃ OC₂H₅ 1341 — O C₃H₇ (6-)OCH₃ O CH₃ OC₂H₅ 1342 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O CH₃ OC₂H₅ 1343 — O C₂H₅ (6-)OC₂H₅ O CH₃ OC₂H₅ 1344 — O C₄H₉ (6-)OC₄H₉ O CH₃ OC₂H₅ 1345 — O CH(CH₃)C₂H₅ (6-)OCH₃ O CH₃ CH₃ 157 1346 — O CH(CH₃)C₂H₅ (6-)OCH₃ O CH₃ C₃H₇ 86 1347 — O CH₂CH(CH₃)₂ (6-)OC₂H₅ O CH₃ Br 108 1348 — O CH₂CH(CH₃)₂ (6-)OC₂H₅ O CH₃ CH₃ 82 1349 — O CH₂CH(CH₃)₂ (6-)OC₂H₅ O

Br 120 1350 — O C₃H₇ (6-)OCH₃ O

OCH(CH₃)₂ 141 1351 — O C₃H₇ (6-)OCH₃ O

OC₃H₇ 102 1352 — O C₂H₅ (6-)OC₂H₅ O

OCH(CH₃)₂ 110 1353 — O C₂H₅ (6-)OC₂H₅ O

OC₃H₇ 132 1354 — O C₂H₅ (6-)OC₂H₅ O

OCH₂CF₃ 114 1355 — O CH(CH₃)₂ (6-)OCH₃ O

OCH(CH₃)₂ 172 1356 — O CH(CH₃)₂ (6-)OCH₃ O

OC₃H₇ 156 1357 — O C₃H₇ (6-)OC₃H₇ O

OCH(CH₃)₂ 141 1358 — O C₂H₅ (6-)OCH₃ O

OC₃H₇ 134 1359 — O C₂H₅ (6-)OC₃H₇ O

OCH(CH₃)₂ 132 1360 — O CH(CH₃)₂ (6-)OC₂H₅ O

OCH(CH₃)₂ 147 1361 — O (CH₂)₂OC₃H₇ (6-)OCH₃ O

OCH₂CF₃ 134 1362 — O CH₂CH (CH₃)₂ (6-)OC₂H₅ O

OCH(CH₃)₂ 96 1363 — O C₃H₇ (6-)OC₂H₅ O

OCH₃ 120 1364 — O CH(CH₃)₂ (6-)OC₂H₅ O

OCH₃ 108 1365 — O CH(CH₃)₂ (6-)OC₂H₅ O

OC₃H₇ 127 1366 — O C₄H₉ (6-)OC₄H₉ O

OCH₃ 118 1367 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O

154 1368 — O C₃H₇ (6-)OCH₃ O

CH₃ 122 1369 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O

CH₃ 134 1370 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O CH₃ CH(CH₃)C₂H₅ 97 1371 — O C₃H₇ (6-)OCH₃ O CH₃ CH(CH₃)₂ 76 1372 — O C₃H₇ (6-)OCH₃ O CH₃ SC₂H₅ 91 1373 — O C₂H₅ (6-)OC₂H₅ O

102 1374 — O C₂H₅ (6-)OC₂H₅ O

CH₃ 125 1375 — O C₂H₅ (6-)OC₂H₅ O

C₂H₅ 112 1376 — O C₂H₅ (6-)OC₂H₅ O

C₃H₇ 113 1377 — O C₂H₅ (6-)OC₂H₅ O CH₃ CH(CH₃)C₂H₅ 100 1378 — O C₂H₅ (6-)OC₂H₅ O CH₃ CH(CH₃)₂ 118 1379 — O C₂H₅ (6-)OC₂H₅ O CH₃ C₄H₉ 81 1380 — O C₂H₅ (6-)OC₂H₅ O CH₃ CH₂CH(CH₃)₂ 93 1381 — O C₃H₇ (6-)OCH₃ O CH₃ CH(CH₃)C₂H₅ 79 1382 — O C₃H₇ (6-)OCH₃ O CH₃ CH₂CH(CH₃)₂ 83 1383 — O C₂H₅ (6-)OC₂H₅ O

OC₂H₅ 67 1384 — O C₂H₅ (6-)OC₂H₅ O

C₃H₇ 105 1385 — O C₂H₅ (6-)OC₂H₅ O

OCH(CH₃)₂ 97 1386 — O C₃H₇ (6-)OCH₃ O

OCH(CH₃)₂ 82 1387 — O C₂H₅ (6-)OC₂H₅ O

CH₂CH(CH₃)₂ 103 1388 — O C₃H₇ (6-)OCH₃ O

CH₂CH(CH₃)₂ 116 1389 — O C₂H₅ (6-)OC₂H₅ O

OCH₃ 104 1390 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O

OCH₃ 127 1391 — O C₃H₇ (6-)OCH₃ O

OCH₃ 93 1392 — O C₂H₅ (6-)OC₂H₅ O

OC₃H₇ 107 1393 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O

OC₃H₇ 130 1394 — O C₃H₇ (6-)OCH₃ O

OC₃H₇ 80 1395 — O C₂H₅ (6-)OC₂H₅ O

C₄H₉ 77 1396 — O C₃H₇ (6-)CH₃ O

C₄H₉ 107 1397 — O C₂H₅ (6-)OC₂H₅ O

107 1398 — O C₃H₇ (6-)OCH₃ O

85 1399 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O

C₄H₉ 89 1400 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O

100 1401 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O CH₃ CH(CH₃)₂ 118 1402 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O CH₃ C₄H₉ 82 1403 — O C₃H₇ (6-)OCH₃ O CH₃ C₄H₉ 75 1404 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O

CH₂CH(CH₃)₂ 95 1405 — O C₂H₅ (6-)OC₂H₅ O CH₃ C(CH₃)═CH₂ 118 1406 — O CH(CH₃)₂ (6-)OCH(CH₃)₂ O CH₃ C(CH₃)═CH₂ 103 1407 — O C₃H₇ (6-)OCH₃ O CH₃ C(CH₃)═CH₂ 92 1408 — O C₃H₇ (6-)OH O CH₃ OC₂H₅ 152 1409 — O C₃H₇ (6-)OH O CH₃ OCH₃ 137 1410 — O C₃H₇ (6-)OH O CH₃ OC₃H₇ 88 1411 — O C₃H₇ (6-)OH O CH₃ OCH(CH₃)₂ 125 1412 — O CH₃ (6-)OH O CH₃ OCH₃ 148 1413 — O CH₃ (6-)OH O CH₃ OC₂H₅ 144 1414 — O CH₃ (6-)OH O CH₃ OC₃H₇ 128 1415 — O CH₃ (6-)OH O CH₃ OCH(CH₃)₂ 158 1416 — O CH₃ (6-)OH O

OCH(CH₃)₂ 137 1417 — O CH₃ (6-)OH O

OC₂H₅ 125 1418 — O CH₃ (6-)OH O C₂H₅ OCH₃ 137 1419 — O CH₃ (6-)OH O CH₃ SCH₃ 130 1420 — O CH₃ (6-)OH O CH₃ C₂H₅ 40 1421 — O C₃H₇ (6-)OCHF₂ O CH₃ OC₂H₅ 230 1422 — O CH₃ (6-)OCHF₂ O CH₃ OC₂H₅ 202 1423 — O CH₃ (6-)OCHF₂ O CH₃ SCH₃ 202 1424 — O CH₃ (6-)OCHF₂ O CH₃ C₂H₅ 98 1425 — S C₃H₇ (6-)OCHF₂ O CH₃ OC₃H₇ 198 1426 — O C₃H₇ (6-)OCHF₂ O

OC₂H₅ 124 1427 — O CHF₂ (6-)OCHF₂ O CH₃ OCH₃ 145 1428 — O CHF₂ (6-)OCHF₂ O CH₃ OC₂H₅ 177 1429 — O CHF₂ (6-)OCHF₂ O CH₃ OC₂H₅ >220 1430 — O CHF₂ (6-)OCHF₂ O

OC₂H₅ 148 1431 — O CHF₂ (6-)OCHF₂ O CH₃ C₂H₅ 123 1432 — O CHF₂ (6-)OCHF₂ O CH₃ SCH₃ 133 1433 — O CHF₂ (6-)OCHF₂ O

CH(CH₃)₂ 130 1434 — O C₃H₇ (6-)OCHF₂ O CH₃ OCH(CH₃)₂ 1435 — O CH₂CH═CH₂ (6-)OC₂H₅ O

OC₂H₅ 84 1436 — O CH₂CH═CH₂ (6-)OC₂H₅ O

OCH₃ 120 1437 — O CH₂CH═CH₂ (6-)OC₂H₅ O CH₃ OCH(CH₃)₂ 133 1438 — O CH₂CH═CH₂ (6-)OC₂H₅ O CH₃ C₂H₅ 137 1439 — O CH₂CH═CH₂ (6-)OC₂H₅ O CH₃ OC₂H₅ 100 1440 — O CH₂CH═CH₂ (6-)OC₂H₅ O CH₃ OCH₃ 94 1441 — O CH₃ (6-)OCH₃ O CH₃ N(CH₃)₂ 168 1442 — O CH₃ (6-)C₂H₅ O CH₃ N(CH₃)₂ 172 1443 — O CF₃ (6-)C₂H₅ O CH₃ N(CH₃)₂ 128 1444 — O CF₃ (6-)CH₃ O CH₃ OC₂H₅ 224 1445 — O CH₃ (6-)OCH₃ O OCH₃ SCH₃ 157 1446 — O CH₃ (6-)OCH₃ O OCH₃ SC₂H₅ 149 1447 — O CH₃ (6-)OCH₃ O OC₂H₅ SCH₃ 147 1448 — O CH₃ (6-)OCH₃ O OC₂H₅ SC₂H₅ 124 1449 — O CH₃ (6-)C₂H₅ O NH₂ CH₃ 204 1450 — O C₂H₅ (6-)OC₂H₅ O OCH₃ SCH₃ 130 1451 — O C₂H₅ (6-)OC₂H₅ O OCH₃ SC₂H₅ 112 1452 — O C₂H₅ (6-)OC₂H₅ O OC₂H₅ SCH₃ 113 1453 — O OC₂H₅ (6-)OC₂H₅ O OC₂H₅ SC₂H₅ 157 1454 — O CF₂CF₂H (6-)CH₃ O CH₃ OCH₃ 127 1455 — O CF₂CF₂H (6-)CH₃ O CH₃ OC₂H₅ 156 1456 — O CF₂CF₂H (6-)CH₃ O CH₃ OC₃H₇ 132 1457 — O CF₂CF₂H (6-)CH₃ O CH₃ OCH(CH₃)₂ 172 1458 — O CF₂CF₂H (6-)CH₃ O CH₃ C₃H₇ 90 1459 — O CF₃ (6-)C₂H₅ O CH₃ OC₃H₇ 185 1460 — O CF₃ (6-)C₂H₅ O CH₃ OCH(CH₃)₂ 192 1461 — O CF₃ (6-)C₂H₅ O CH₃ OCH₂CF₃ 159 1462 — O CF₃ (6-)C₂H₅ O CH₃

192 1463 — O CF₃ (6-)C₂H₅ O CH₃ CH₃ >270 1464 — O CF₃ (6-)C₂H₅ O CH₃ C₂H₅ 259 1465 — O CF₃ (6-)C₂H₅ O CH₃ C₃H₇ 241 1466 — O CF₃ (6-)C₂H₅ O CH₃ SCH₃ 174 1467 — O CF₃ (6-)C₂H₅ O

OCH₃ 165 1468 — O CF₃ (6-)C₂H₅ O

OC₂H₅ 145 1469 — O CF₃ (6-)C₂H₅ O

OC₃H₇ 196 1470 — O CF₃ (6-)C₂H₅ O

OCH(CH₃)₂ 170 1471 — O CF₃ (6-)C₂H₅ O

OCH₂CF₃ 183 1472 — O CF₃ (6-)C₂H₅ O

154 1473 — O CF₃ (6-)C₂H₅ O CH₃

188 1474 — O CF₃ (6-)C₂H₅ O

C₂H₅ 163 1475 — O CF₃ (6-)C₂H₅ O

C₃H₇ 190 1476 — O CF₃ (6-)C₂H₅ O

SCH₃ 159 1477 — O CF₃ (6-)C₂H₅ O

CH₃ 151 1478 — O CF₃ (6-)C₂H₅ O

C₃H₇ 163 1479 — O CF₃ (6-)C₂H₅ O

CH═CH(CH₃) 176 1480 — O CF₃ (6-)C₂H₅ O

156 1481 — O CF₃ (6-)C₂H₅ O

CH₂OCH₃ 146 1482 — O CH₃ (6-)C₂H₅ O OCH₃ SCH₃ 149 1483 — O CH₃ (6-)C₂H₅ O OCH₃ SC₂H₅ 137 1484 — O CH₃ (6-)C₂H₅ O OC₂H₅ SCH₃ 115 1485 — O CH₃ (6-)C₂H₅ O OC₂H₅ SC₂H₅ 99 1486 — O CH(CH₃)₂ (6-)CH₃ O

CH(CH₃)₂ 132 1487 — O CF₃ (6-)C₂H₅ O

CH(CH₃)₂ 108 1488 — O CH₃ (6-)C₂H₅ O

CH(CH₃)₂ 151 1489 — O CH₃ (6-)OCH₃ O

CH(CH₃)₂ 163 1490 — O C₂H₅ (6-)OC₂H₅ O

CH(CH₃)₂ 111 1491 — O CH₃ (6-)C₂H₅ O CH₃

118 1492 — O CH₃ (6-)C₂H₅ O

147 1493 — O CF₃CF₃H (6-)CH₃ O

OCH₃ 160 1494 — O CF₃CF₃H (6-)CH₃ O

OC₂H₅ 155 1495 — O CF₃CF₃H (6-)CH₃ O

OCH(CH₃)₂ 166 1496 — O CH₂CF₃ (6-)CH₃ O CH₃ OCH₃ 149 1497 — O CH₂CF₃ (6-)CH₃ O CH₃ OC₂H₅ 230 1498 — O CH₂CF₃ (6-)CH₃ O CH₃ OC₃H₇ 238 1499 — O CH₂CF₃ (6-)CH₃ O CH₃ OCH(CH₃)₂ 89 1500 — O CH₂CF₃ (6-)CH₃ O CH₃

134 1501 — O CH₂CF₃ (6-)CH₃ O

OCH₃ 189 1502 — O CH₂CF₃ (6-)CH₃ O

OC₂H₅ 129 1503 — O CH₂CF₃ (6-)CH₃ O

OC₃H₇ 126 1504 — O CH₂CF₃ (6-)CH₃ O

OCH(CH₃)₂ 161 1505 — O CH₂CF₃ (6-)CH₃ O

128 1506 — O CH₂CF₃ (6-)CH₃ O CH₃ C₃H₇ 148 1507 — O CH₃ (6-)C₂H₅ O CH₃

144 1508 — O CH₃ (6-)C₂H₅ O CH₃ CH═CH(CH₃) 138 1509 — O CH₃ (6-)C₂H₅ O CH₃

160 1510 — O CH₃ (6-)C₂H₅ O

CH₃ 168 1511 — O CH₃ (6-)C₂H₅ O

C₂H₅ 143 1512 — O CH₃ (6-)C₂H₅ O

C₃H₇ 140 1513 — O CH₃ (6-)C₂H₅ O

170 1514 — O CH₃ (6-)C₂H₅ O

CH═CH(CH₃) 127 1515 — O CH₃ (6-)C₂H₅ O

N(CH₃)₂ 214 1516 — O CH₃ (6-)C₂H₅ O

SCH₃ 167 1517 — O CH₃ (6-)C₂H₅ O

SC₂H₅ 137 1518 — O CH₃ (6-)C₂H₅ O

OCH₃ 165 1519 — O CH₃ (6-)C₂H₅ O

OCH₂CF₃ 163 1520 — O CH₃ (6-)C₂H₅ O

OC₃H₇ 125 1521 — O CH₃ (6-)C₂H₅ O

133 1522 — O CH₃ (6-)C₂H₅ O CH₃

136 1523 — O CF₂H (6-)C₂H₅ O CH₃ OCH₃ 121 1524 — O CF₂H (6-)C₂H₅ O CH₃ OC₂H₅ 150 1525 — O CF₂H (6-)C₂H₅ O CH₃ OC₃H₇ 119 1526 — O CF₂H (6-)C₂H₅ O CH₃ OCH(CH₃)₂ 122 1527 — O CF₂H (6-)C₂H₅ O CH₃

146 1528 — O CF₂H (6-)C₂H₅ O

OCH₃ 163 1529 — O CF₂H (6-)C₂H₅ O

OC₂H₅ 140 1530 — O CF₂H (6-)C₂H₅ O

OC₃H₇ 129 1531 — O CF₂H (6-)C₂H₅ O

OCH(CH₃)₂ 118 1532 — O CF₂H (6-)C₂H₅ O

133 1533 — O CH₂CH₂F (6-)C₂H₅ O CH₃ CH₃ 290 1534 — O CH₂CH₂F (6-)C₂H₅ O CH₃ C₃H₇ 274 1535 — O CH₂CH₂F (6-)C₂H₅ O OC₂H₅ C₂H₅ 118 1536 — O CH₂CH₂F (6-)C₂H₅ O CH₃ N(CH₃)₂ 170 1537 — O CH₂CH₂F (6-)C₂H₅ O CH₃ SCH₃ 168 1538 — O CH₂CH₂F (6-)C₂H₅ O CH₃ OCH₃ 166 1539 — O CH₂CH₂F (6-)C₂H₅ O CH₃ OC₂H₅ 140 1540 — O CH₂CH₂F (6-)C₂H₅ O CH₃ OC₃H₇ 138 1541 — O CH₂CH₂F (6-)C₂H₅ O CH₃ OCH(CH₃)₂ 136 1542 — O CH₂CH₂F (6-)C₂H₅ O CH₃

139 1543 — O CH₂CH₂F (6-)C₂H₅ O

OCH₃ 156 1544 — O CH₂CH₂F (6-)C₂H₅ O

OC₂H₅ 138 1545 — O CH₂CH₂F (6-)C₂H₅ O

OC₃H₇ 125 1546 — O CH₂CH₂F (6-)C₂H₅ O

OCH(CH₃)₂ 140 1547 — O CH₂CH₂F (6-)C₂H₅ O

158 1548 — O CH₃ (6-)C₂H₅ O

C₅H₉ 149 1549 — O CH₃ (6-)C₂H₅ O CH₃ C₅H₉ 118 1550 — O CF₃ (6-)C₃H₇ O CH₃ OCH₃ 94 1551 — O CF₃ (6-)C₃H₇ O CH₃ OC₂H₅ 175 1552 — O CF₃ (6-)C₃H₇ O CH₃ OC₃H₇ 166 1553 — O CF₃ (6-)C₃H₇ O CH₃ OCH(CH₃)₂ 164 1554 — O CF₃ (6-)C₃H₇ O CH₃ OCH₂CF₃ 221 1555 — O CF₃ (6-)C₃H₇ O CH₃

189 1556 — O CF₃ (6-)C₃H₇ O

OCH₃ 182 1557 — O CF₃ (6-)C₃H₇ O

OCH₂CH₃ 134 1558 — O CF₃ (6-)C₃H₇ O

OC₃H₇ 207 1559 — O CF₃ (6-)C₃H₇ O

OCH(CH₃)₂ 148 1560 — O CF₃ (6-)C₃H₇ O

OCH₂CF₃ 204 1561 — O CF₃ (6-)C₃H₇ O

186 1562 — O CH₃ (6-)C₂H₅ O CH₂CH₂OCH₂ 163 1563 — O CH₃ (6-)C₂H₅ O CH₂CH₂CH₂OCH₂ 191 1564 — O CF₃ (6-)CH₃ O

OCH₃ 197 1565 — O CH₂CF₂H (6-)CH₃ O CH₃ OCH₃ 231 1566 — O CH₂CF₂H (6-)C₂H₅ O CH₃ OCH₃ 174 1567 — O CH₂CF₂H (6-)C₂H₅ O

OCH₃ 160 1568 — O CH₂CF₂H (6-)C₂H₅ O

OCH(CH₃)₂ 162 1569 — O CH₂CF₂H (6-)C₂H₅ O CH₃ CH₃ >250 1570 — O CH₂CF₂H (6-)CH₃ O CH₃ OCH₂CF₃ 117 1571 — O CH₂CF₂H (6-)CH₃ O CH₃

128 1572 — O CH₂CF₂H (6-)CH₃ O

124 1573 — O CH₂CF₂H (6-)CH₃ O CH₃ C₂H₅ 137 1574 — O CH₂CF₂H (6-)CH₃ O CH₃ C₃H₇ 139 1575 — O CH₂CF₂H (6-)CH₃ O CH₃

150 1576 — O CH₂CF₂H (6-)CH₃ O CH₃ CH₂OCH₃ 114 1577 — O CH₂CF₂H (6-)CH₃ O CH₃ SCH₃ 155 1578 — O CH₂CF₂H (6-)C₃H₇ O CH₃ CH₃ 290 1579 — O CH₂CF₂H (6-)CH₃ O CH₃ N(CH₃)₂ 116 1580 — O CH₂CF₂H (6-)CH₃ O OC₂H₅ C₂H₅ 125 1581 — O CH₂CF₂H (6-)CH₃ O

CH₃ 137 1582 — O CH₂CF₂H (6-)CH₃ O

OC₂H₅ 99 1583 — O CH₂CF₂H (6-)CH₃ O

OC₃H₇ 130 1584 — O CH₂CF₂H (6-)C₂H₅ O CH₃ OC₂H₅ 147 1585 — O CH₂CF₂H (6-)C₂H₅ O CH₃ OCH(CH₃)₂ 151 1586 — O CH₃ (6-)C₂H₅ O CH₃ N(CH₃)₂ 199 1587 — O CF₃ (6-)C₂H₅ O CH₃ CH═CH(CH₃) 128 1588 — O CF₃ (6-)C₂H₅ O CH₃ CH₂OCH₃ 101 1589 — O CF₃ (6-)C₂H₅ O

N(CH₃)₂ 154 1590 — O CF₃ (6-)C₂H₅ O

SC₂H₅ 143 1591 — O CF₃ (6-)C₂H₅ O CH₃ SC₂H₅ 113 1592 — O CF₃ (6-)C₂H₅ O OC₂H₅ C₂H₅ 122 1593 — O CF₃ (6-)C₂H₅ O OC₂H₅ SC₂H₅ 133 1594 — O CF₃ (6-)C₂H₅ O CH₃ OC₆H₅ 193 1595 — O CH₂CH₂F (6-)CH₃ O CH₃ C₂H₅ 109 1596 — O CH₂CH₂F (6-)CH₃ O CH₃

157 1597 — O CH₂CH₂F (6-)CH₃ O CH₃ CH₂OCH₃ 106 1598 — O CH₂CH₂F (6-)CH₃ O CH₃ SCH₃ 135 1599 — O CH₂CH₂F (6-)CH₃ O CH₃ N(CH₃)₂ 141 1600 — O CH₂CH₂F (6-)CH₃ O OC₂H₅ C₂H₅ 129 1601 — O CH₂CH₂F (6-)CH₃ O

CH₃ 169 1602 — O CH₂CH₂F (6-)CH₃ O

OC₂H₅ 125 1603 — O CH₂CH₂F (6-)CH₃ O

OC₃H₇ 117 1604 — O CH₂CH₂F (6-)CH₃ O CH₃

145 1605 — O CH₂CH₂F (6-)CH₃ O

118 1606 — O CH₂CH₂CH₂F (6-)C₃H₇ O CH₃ OCH₃ 127 1607 — O CH₂CH₂CH₂F (6-)C₃H₇ O CH₃ OCH(CH₃)₂ 155 1608 — O CH₂CH₂CH₂F (6-)C₃H₇ O

OCH₃ 106 1609 — O CH₂CH₂CH₂F (6-)C₃H₇ O

OCH(CH₃)₂ 138 1610 — O CH₂CH₂F (6-)C₂H₅ O CH₃

157 1611 — O CH₂CH₂F (6-)C₂H₅ O CH₃ CH₂OCH₃ 101 1612 — O CH₂CH₂F (6-)C₂H₅ O

CH₃ 147 1613 — O CH₂CH₂F (6-)CH₃ O CH₃ C₃H₇ 280 1614 — O CH₂CH₂CH₂F (6-)C₃H₇ O CH₃ CH₃ 302 1615 — O CH₂CH₂CH₂F (6-)C₃H₇ O CH₃ C₃H₇ 261 1616 — O CH₂CH₂F (6-)C₃H₇ O CH₃ C₃H₇ 108 1617 — O CH₂CH₂F (6-)C₃H₇ O CH₃ OCH₃ 158 1618 — O CH₂CH₂F (6-)C₃H₇ O CH₃ OC₂H₅ 152 1619 — O CH₂CH₂F (6-)C₃H₇ O CH₃ OCH(CH₃)₂ 164 1620 — O CH₂CH₂F (6-)C₃H₇ O

OCH₃ 137 1621 — O CH₂CH₂F (6-)C₃H₇ O

OC₂H₅ 117 1622 — O CH₂CH₂F (6-)C₃H₇ O

OCH(CH₃)₂ 158 1623 — O CH₂CH₂F (6-)C₃H₇ O CH₃ N(CH₃)₂ 147 1624 — O CH₂CH₂F (6-)C₃H₇ O OC₂H₅ C₂H₅ 237 1625 — O CH₂CH₂F (6-)C₃H₇ O CH₃ SCH₃ 130 1626 — O CHF₂ (6-)Br O CH₃ OCH₃ 160 1627 — O CHF₂ (6-)Br O CH₃ CH₃ 146 1628 — O CHF₂ (6-)Br O CH₃ C₃H₇ 127 1629 — O CHF₂ (6-)Br O CH₃ OC₂H₅ 168 1630 — O CHF₂ (6-)Br O CH₃ OCH(CH₃)₂ 126 1631 — O CHF₂ (6-)Br O

OCH₃ 145 1632 — O CHF₂ (6-)Br O

OC₂H₅ 125 1633 — O CHF₂ (6-)Br O

OCH(CH₃)₂ 148 1634 — O CHF₂ (6-)Br O CH₃ N(CH₃)₂ 173 1635 — O CF₃ (6-)F O CH₃ SCH₃ 1636 — O CF₃ (6-)F O CH₃ C₂H₅ 1637 — O CF₃ (6-)F O CH₃ OC₂H₅

The compound listed in Table 1 as Example 9 can be prepared, for example, as follows:

(Process (b))

1.4 g (0.01 mol) of 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one and 2.4 g (0.01 mol) of 2-ethoxy-6-methyl-phenylsulphonyl isocyanate are stirred at 20° C. for 15 hours in 50 ml of acetonitrile. The solvent is distilled off, the residue is stirred with diethyl ether and the precipitate is filtered off with suction.

3.3 g (85% of theory) of 5-ethoxy-4-methyl-2-(2-ethoxy-6-methyl-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 160° C.

Starting Materials of the Formula (II) or (IIa):

Example (II-1)

64.6 g (0.26 mol) of 2-isopropoxy-6-methyl-benzenesulphochloride are stirred at 20° C. for 12 hours in 350 ml of 25% strength aqueous ammonia solution. The crystalline product is subsequently isolated by filtration with suction.

54 g (90% of theory) of 2-isopropoxy-6-methyl-benzenesulphonamide are obtained of melting point 78° C.

Example (II-2)

A mixture of 1.9 g (10 mmol) of 2-hydroxy-6-methyl-benzenesulphonamide, 1.2 g (10 mmol) of propargyl bromide (in the form of an 80% strength solution in toluene) and 1.4 g (10 mmol) of potassium carbonate is heated under reflux for 2 hours. The mixture is then filtered, the filtrate is concentrated under a water pump vacuum, the residue is digested with petroleum ether and the crystalline product obtained from this digestion is isolated by filtration with suction.

2.1 g (93% of theory) of 6-methyl-2-propargyloxy-benzenesulphonamide are obtained of melting point 129° C.

Example (II-3)

188 ml of a 1-molar solution of boron(III) bromide in methylene chloride are added dropwise at 20° C. with stirring to a solution of 32.3 g (0.15 mol) of 2-ethoxy-6-methylbenzenesulphonamide in 300 ml of methylene chloride, and the reaction mixture is stirred at 20° C. for 30 minutes. Then 300 ml of methanol are added dropwise at from 0° C. to 5° C. (ice cooling). After heating to 20° C., the reaction mixture is concentrated under a water pump vacuum and the residue is stirred with ethyl acetate. The solution obtained is washed with water, dried over sodium sulphate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is crystallized by stirring with petroleum ether, and the crystalline product is isolated by filtration with suction.

20.3 g (72% of theory) of 2-hydroxy-6-methyl-benzenesulphonamide are obtained of melting point 126° C.

In analogy to Examples (II-1) to (II-3) and in accordance with the general description of the preparation process according to the invention, it is also possible, for example, to prepare the compounds of the formula (II) or (IIa) listed in Table 2 below.

TABLE 2 Examples of the compounds of the formula (II) (position-) Melting Ex. No. A R¹ R² point (° C.) II-4 — C₂H₅ (6-)CH₃ 104 II-5 — n-C₃H₇ (6-)CH₃ 63 II-6 — —CH₂CH₂Cl (6-)CH₃ 102 II-7 — CH₃ (6-)CH₃ 132 II-8 — —CH₂C₆H₅ (6-)CH₃ 131 II-9 — —CH₂COOCH₃ (6-)CH₃ 90 II-10 — CH₃ (6-)C₃H₇-n 108 II-11 — C₂H₅ (6-)C₃H₇-n 80 II-12 — C₂H₅ (5-)CH₃ 131 II-13 — CH₃ (6-)Cl 166 II-14 — C₂H₅ (6-)Cl 121 II-15 — H (6-)Cl 118 II-16 — i-C₃H₇ (6-)Cl 85 II-17 — —CH₂CH=CH₂ (6-)Cl 106 II-18 — —CH₂C≡CH (6-)Cl 181 II-19 — CF₃ (5-)Cl II-20 — CHF₂ (5-)CH₃ 127 II-21 — CHF₂ (6-)CH₃ 89 II-22 — CH₃ (5-)C(CH₃)₃ 160 II-23 — CH₃ (5-)Cl II-24 — CHF₂ (4-)CH₃ 153 II-25 — —CF₂CHFCl (6-)CH₃ 85 II-26 — C₂H₅ (6-)CH₂Cl

Starting Materials of the Formula (IV):

Example (IV-1)

21.5 g (0.1 mol) of 2-ethoxy-6-methyl-benzenesulphonamide and 10 g (0.1 mol) of n-butyl isocyanate are heated to boiling in 100 ml of chlorobenzene. At reflux temperature, phosgene is passed in for 4 hours. The clear solution is concentrated under reduced pressure and the residue is subjected to precision distillation. At a pressure of 0.8 mbar and an overhead temperature of 135-140° C., 2-ethoxy-6-methyl-phenylsulphonyl isocyanate goes over and solidifies in the receiver.

7.9 g of 2-ethoxy-6-methyl-phenylsulphonyl isocyanate are obtained as a colourless product of melting point 40° C.

Starting Materials of the Formula (VI) or (VIa):

Example (VI-1)

47.8 g (0.29 mol) of 2-isopropoxy-6-methyl-aniline are dissolved in a mixture of 87 ml of IN hydrochloric acid and 145 ml of conc. hydrochloric acid, and the solution is cooled to −5° C. At −5° C. to 0° C., a solution of 22 g (0.32 mol). of sodium nitrite in 87 ml of water is then added dropwise with stirring and the mixture is stirred at about 0° C. for a further hour. After removal of the nitrite excess with amidosulphonic acid, the diazonium salt solution obtained is added dropwise at −5° C. to 0° C. to a saturated solution of sulphur dioxide in 175 ml of 1,2-dichloro-ethane. After about 30 minutes, 1.7 g of copper(I) chloride and 1.7 g of dodecyl-trimethylammonium bromide are added, and the reaction mixture is allowed to rise to room temperature over the course of about 60 minutes, heated to about 40° C. over a further hour, and stirred at this temperature for about 12 hours. At about 20° C., 14.2 g of a 35% strength hydrogen peroxide solution are then added and the mixture is stirred for about 30 minutes. It is subsequently stirred with 300 ml of methylene chloride, and the organic phase is separated off, washed with water, dried over sodium sulphate and filtered. The solvent is carefully removed from the filtrate by distillation under a water pump vacuum.

65.9 g (90% of theory) of 2-isopropoxy-6-methyl-benzenesulphochloride are obtained as a brownish oily residue.

¹H-NMR (CDCl₃, TMS, δ ppm): 1.47 (d, J=6.1 Hz, 2xCH₃); 2.68 (s, CH₃); 4.79 (sept., J=6.1 Hz, 1H); 6.83 (d, J=7.5 Hz, 1H); 6.95 (d, J=8.4 Hz, 1H); 7.45 (pseudo t, J=8.3 Hz, 1H).

In analogy to Example (VI-I) it is also possible, for example, to prepare the compounds of the formula (VI) or (VIa) listed in Table 3 below.

TABLE 3 (VI)

Examples of the compounds of the formula(VI) (position-) Physical Ex. No. A R¹ R² data VI-2 — CH₃ (6-)CH₃ Fp.: 52° C. VI-3 — C₂H₅ (6-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 1,55 (t, J=6,97 Hz, CH₃), 2,69(s, CH₃), 4,24(q, J=6,97 Hz, CH₂), 6,87(d, J=7,68 Hz, 1H), 6,95(d, J=8,34 Hz, 1H), 7,46(pseudo t, J=8,1 Hz, 1H) VI-4 — n-C₃H₇ (6-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 1,33 (t, J=7,38 Hz, CH₃), 1,95(m, CH₂), 2,69(s, CH₃), 4,12(t, J=6,3 Hz, CH₂), 6,86(d, J=7,69 Hz, 1H), 6,94 (d, J=8,37 Hz, 1H), 7,46(pseudo t, J=7,8 Hz, 1H) VI-5 — —CH₂CH₂Cl (6-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 2,71 (s, CH₃), 3,94(t, J=6,1 Hz, CH₂), 4,41(t, J=6, 1 Hz, CH₂), 6,96(t, J=7, 1 Hz, 2H), 7,5(t, J=7,8 Hz, 1H) VI-6 — —CH₂CH₂OC₂H₅ (6-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 1,23 (t, J=7 Hz, CH₃), 2,69(s, CH₃), 3,65 (q, J=7 Hz, CH₂), 3,91(t, J=5,16 Hz CH₂), 4,30(t, J=5,16 Hz, CH₂), 6,89 (d, J=7,7 Hz, 1H), 7,0(d, J=8,3 Hz 1H), 7,47(pseudo t, J=8,1 Hz, 1H) VI-7 — C₂H₅ (5-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 1,53 (t, J=7 Hz, CH₃), 2,36(s, CH₃), 4,25 (q, J=7 Hz, CH₂), 7,0(d, J=8,53 Hz, 1H), 7,45(d, J1=8,53 Hz, J2=2,15 Hz, 1H), 7,75(d, J=2,15 Hz, 1H) VI-8 — n-C₃H₇ (5-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 1,08 (t, J=7,38 Hz, CH₃), 1,85(m, CH₂), 2,23(s, CH₃), 3,99(t, J=6,5 Hz), 6,74 (d, J=8,2 Hz, 1H), 6,92(m, 1H), 7,34 (d, J=1,65 Hz, 1H) VI-9 — i-C₃H₇ (5-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 1,45 (d, J=6,06, 2xCH₃), 2,35(s,CH₃), 4,77(sept., J=6,06 Hz, 1H), 6,99(d, J=8,57 Hz, 1H), 7,43(dd, J1=8,56 Hz, 1H, J2=2,1 Hz, 1H), 7,74(d, J=2,1 Hz, 1H) VI-10 — C₂H₅ (6-)CH₂Cl (Oil) VI-11 — —CF₂CHFCl (6-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 2,78 (s, CH₃), 6,46(td, CHFCl), 7,2-7,6 (Ar—H) VI-12 — CHF₂ (6-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 2,76 (s, CH₃), 6,61(t, CHF₂), 7,27-7,59 (Ar—H) VI-13 — CH₃ (5-)C(CH₃)₃ Fp.: 62° C. VI-14 — CHF₂ (4-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 2,50 (s, CH₃), 6,68(t, CHF₂), 7,05-7,92 (Ar—H) VI-15 — CHF₂ (5-)CH₃ ¹H-NMR(CDCl₃, TMS, δ, ppm): 2,45 (s, CH₃), 6,64(t, CHF₂), 7,35-7,86 (AR—H) VI-16 — —CH₂CH₂Cl (6-)CH₃ VI-17 — —CH₂CH═CH₂ (6-)CH₃ VI-18 — —CH₂C≡CH (6-)CH₃ VI-19 — —CH₂C₆H₅ (6-)CH₃

Startiniz Materials of the Formula (X) Example (X-1)

Step 1: Preparation of 2-Isopropoxy-6-methyl-nitrobenzene

A mixture of 153 g (1.0 mol) of 3-methyl-2-nitro-phenol, 172.5 g (1.25 mol) of potassium carbonate, 170 g (1.0 mol) of 2-iodo-propane and 400 ml of acetone is heated under reflux for 12 hours. It is subsequently concentrated under a water pump vacuum, the residue is stirred with 400 ml of methylene chloride, the mixture is filtered and the filter product is washed with methylene chloride. The solvent is removed carefully from the filtrate by distillation under a water pump vacuum.

183.4 g of 2-isopropoxy-6-methyl-nitrobenzene are obtained as a yellow oily residue.

¹H-NMR (CDCl₃, TMS, δ, ppm): 1.33 (d, J=6.1 Hz, 2xCH₃), 2.28 (s, CH₃), 4.6 (sept., J=6.1 Hz, 1H), 6.8 (d, J=7.7 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 7.26 (pseudo t, J=8.1 Hz, 1H).

Step 2: Preparation of 2-Isopropoxy-6-methyl-aniline

183.3 g (0.94 mol) of 2-isopropoxy-6-methyl-nitrobenzene are hydrogenated in 1 litre of ethyl acetate in the presence of 9.5 g of Raney nickel under a hydrogen pressure of from 40 to 60 bar for 5 hours. The mixture is then filtered and the solvent is carefully removed from the filtrate by distillation under a water pump vacuum.

139.4 g (90% of theory) of 2-isopropoxy-6-methyl-aniline are obtained as an orange-coloured oily residue.

¹H-NMR (CDCl₃, TMS, δ, ppm): 1.36 (d, J=6.1 Hz, 2xCH₃), 2.16 (s, CH₃), 3.72 (s, NH₂), 4.51 (sept., J=6.1 Hz, 1H), 6.65-6.70 (m, 3H).

Use Examples

In the Use Examples, the compounds specified below are used as comparison substances:

4,5-Dimethoxy-2-(2-methoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (known from EP 534266);

4,5-Diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4dihydro-3H-1,2,4-triazol-3-one (known from EP 534266).

Example A

Pre-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil, and, after 24 hours, the soil is watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive.

After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:

0%=no action (like untreated control) 100%=total destruction

In this test, the compounds according to Preparation Examples 1, 7-21, 23-41, 46-49, 51, 54, 55, 57, 60, 62, 65, 68, 72-74, 76, 78, 79, 88, 89, 199, 207, 209, 222 and 901 for example, exhibit a very strong action against broad-leaved weeds.

Example B

Post-emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 2,000 1 of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control) 100%=total destruction

In this test, the compounds according to Preparation Examples 1, 7-10, 12, 13, 15, 16, 17, 25, 30, 31, 38, 40, 41, 46 and 47, for example, exhibit a very strong action against broad-leaved weeds. 

What is claimed is:
 1. A compound of the formula (II), (IV) or (VI):

wherein A represents a single bond; R¹ represents ethyl substituted by fluoro, chloro, bromo, methoxy or ethoxy, or represents n- or i-propyl, n-, s- or i-butyl, propenyl, butenyl, propinyl or butinyl, each of which is optionally substituted by fluoro, chloro, bromo, methoxy or ethoxy; R² represents cyano, fluoro, chloro or bromo, or represents methyl substituted by fluoro, or represents ethyl, n- or i-propyl, n- or i-propoxy, n- or s-butoxy, each of which is optionally substituted by fluoro, chloro, bromo, methoxy or ethoxy; and R² is in position
 6. 2. A compound of the formula (II), (IV) or (VI):

wherein A represents a single bond; R² is in position 6; and the substituents R¹ and R² are selected according to the following combinations: Combination No. R¹ R² 1 Allyl O—C₂H5 2 CHF₂ Br 3 CHF₂ O—C₃H₇-n 4 CHF₂ CHF₂ 5 CF₃ Br 6 CH₂CH₂—O—C₂H₅ CH₃ 7 CH₃ C₃H₇-i 8 CH₃ C₃H₇-n 9 CH₃ O—C₃H₇-n 10 CH₃ O—C₄H₉-n 11 CH₃ O—C₄H₉-s 12 CH₃ CN 13 C₂H₅ Cl 14 C₂H₅ F 15 C₂H₅ C₂H₅ 16 C₂H₅ O—C₂H₅ 17 C₂H₅ C₃H₇-n 18 C₂H₅ O—C₃H₇-i 19 C₂H₅ O—C₃H₇-n 20 C₂H₅ O-C₄H₉-n 21 H CF₃ 22 C₃H₇-n Cl 23 C₃H₇-n F 24 C₃H₇-n CF₃ 25 C₃H₇-n Br 26 C₃H₇-n C₃H₇-n 27 C₃H₇-n O—CH₂F₂ 28 C₃H₇-i Cl 29 C₃H₇-i CH₃ 30 C₃H₇-i F 31 C₃H₇-i CF₃ 32 C₃H₇-i C₂H₅ 33 C₃H₇-i C₃H₇-i 34 C₃H₇-i O—C₃H₇-i 35 cyclopentyl O—CH₃ 36 CH₂CH₂—Cl CH₃ 37 CH₂CHFCl CH₃ 38 C₄H₉-n CH₃ 39 C₄H₉-i O—CH₃ 40 C₄H₉-i O—C₂H₅ 41 CF₂Cl CH₃ 42 CH₂CH₂F CH₃ 43 CH₂CH₂F CF₃ 44 CH₂CH₂F C₂H₅ 45 C₄H₉-s C₄H₉-s 46 CH₂CHF₂ CH₃ 47 CH₂CHF₂ C₂H₅ 48 CH₂CHF₂ C₃H₇-n 49 CH₂CH₂O—C₃H₇-n O—CH₃ 50 CH₂CH₂CH₂F C₃H₇-n 51 C₄H₉-i CH₃ 